Newbie, Strategy Advice, STR to start and then MTR

[Allison Hertzberg]

Hi everyone, go easy on me! It's been three weeks of drinking from the fire house of real estate investment.  Looking to buy my first property and launch by EOY so looking for something pretty turnkey.  My thought is to start off self managing in 2025 for bonus depreciation against my W2, and then switch in 2026 to MTR so my kids don't feel so neglected (kidding, not kidding :).

My focus to start is tax strategy and taking losses against my W2, then with mid term it would be to avoid headache of turnover and focus on light cashflow and holding for appreciation.

Was thinking Bradenton FL, PCB or Poconos, so i can reach all fairly quickly from the NE.

How difficult is it to switch from STR to MTR and then what are the implications if i did a cost seg in year one and took bonus depreciation, then switched after those 1st year losses?

[Trent Reeve]

Quote from @Allison Hertzberg:

Hi everyone, go easy on me! It's been three weeks of drinking from the fire house of real estate investment.  Looking to buy my first property and launch by EOY so looking for something pretty turnkey.  My thought is to start off self managing in 2025 for bonus depreciation against my W2, and then switch in 2026 to MTR so my kids don't feel so neglected (kidding, not kidding :).

My focus to start is tax strategy and taking losses against my W2, then with mid term it would be to avoid headache of turnover and focus on light cashflow and holding for appreciation.

Was thinking Bradenton FL, PCB or Poconos, so i can reach all fairly quickly from the NE.

How difficult is it to switch from STR to MTR and then what are the implications if i did a cost seg in year one and took bonus depreciation, then switched after those 1st year losses?

 Im in the PCB market. you arent going to find many MTR, so I would be careful on that being your long term strategy there. I would bet similar with the Poconos. Most vacation markets are not generally set up to support MTR's.