Boys Trip - St Petes, 2025
Took Lucas and 4 friends down to St Petes from Friday morning to Monday morning, sitting in the bright and sunny Tampa airport after just being notified that the shitshow Newark airport air traffic control just delayed us for 30 minutes. We shall see what that eventually means.
I’ve traveled with one of Lucas’ friends a lot, 2 quite often too, but Lucas +4 was a bit of an experiment with a lot of extra logistical elements - we couldn’t all fit in one car from home to the airport (solution: took two cars), there was no way 5 large young men were staying at my condo with their dirty and wet shit everywhere (solution:rent a room at the Marriott just around the corner for three of them). They wouldn’t all fit into a regular sized SUV especially when luggage is accounted for (solution:bad ass large oversized Tahoe).
They were all over the place - beach, mall, put dozens of miles or more on rental bikes and scooters, movie theaters, a ton of time on our rooftop pool and jacuzzi and gym. And watched the new Adam Sandler film Happy Gilmore II.
Out of 4 bag search opportunities going through Pre-Check there and back, I got flagged 3 times - 1, for poker chips I was carrying from PA to FL in hopes of teaching the kids some poker (didn’t happen), 2, for a ham sandwich and banana, and 3, for a candle Lucas asked me to carry.
Like up North, but more, it was hot down here, feeling like 105 mid-day. Played pickleball Sunday morning at Crescent Park with the 40 or 50 people who show up to play each morning, 7 days a week. Whack whack whack here the neighbors. The tennis courts adjacent sit unused.
Florida storms are wild, and last night one blew in that packed rain, cool clouds, thunder and a lot of lightening. I’m not sure how much stock to put into it since I’ve only seeing some posts on my TikTok, but they say the Florida real estate market is crashing with a perfect Floridian storm of back to work mandates, natural disasters, insurance costs, condo assessments, higher real estate taxes and too much new supply of single family and condo Units.
On the home front, we just finished the Parksville lakefront home. And when I say finished, I mean wrapped up tight across an array of requirements for an easy landing - certificate of occupancy, utility set ups, bank inspections, paperwork, warranties, walk-throughs and sign-offs. Our lakefront in North Branch is cruising along and our New Paltz Ranch with views is moving along as well. Unlike a lot of our competitors our shit is always moving forward. It’s just my nature.
I’m spending a lot time on trying to decipher the best use of my accumulated capital - be in currently invested in longer term rental real estate, or equity markets. With the 8 un-mortgaged rental homes across 3 states (NY, PA and FL), with the help of CPA John in the office, we are looking at the return on investment ratios on the following fronts - 1, long term rentals, 2, selling and investing the money, 3, selling and holding the mortgages where possible. Lots of tax ramifications that drive the decision-making - in fact the tax consequences factor as a primary concern/variable when evaluating options - ordinary income, capital gains, current tax brackets vs future brackets (typically lower)- trying to find the magic investment sequencing, and also trying to determine if rental real estate outperforms the stock market, etc.. - all complicated because the last 8 years have been such go go good times for investments of all sorts, it’s hard to remember and plan around past results are not indicative of future results.
Though I am getting more comfortable with the idea the stock market will return 7-10% over time, something I’ve always been suspicious of.
Interestingly, and finally, prices on land in SuCo have stabilized and perhaps even retreated from their highest levels. And as important, or relatedly I guess, things aren’t selling the minute they hit the marketplace. This allows us here at Catskill Farms to get a little more serious about ramping up our purchases of land and put up a few more houses. I feel vindicated, if that’s the right word, for sitting on the sidelines for a bit and watching the dust settle. While land is about double at times, and many times more, there are at least now opportunities to pick up some parcels where I’m comfortable with the prices - meaning $50’s, 60’s and maybe even 70’s. For someone buying SuCo land in the $20ks or low $30’s for decades, it takes some getting used to. Sure, end prices are higher, but so is every single ingredient necessary to build a home.
Lucas, far right, worn out from hosting all day long.
And of course no trip is satisfactory unless lucas gets a dumb picture of me.
