Because of this, I am having difficulty measuring what rent would be enough to still cash flow as well as not to price myself out of the market while I'm analyzing properties.

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? 

The only slight difficulty might come if they’re 2-4 units and you need to find comps for your appraisal.

-investing out of state is difficult. 

The verbiage of the conversation (err the difficulty thereof) wasn't the issue but how would the LL and tenant be able to resolve issues in the future? 

( difficulty reselling the unit, and it has a small percentage risk on your health)I would like to know if the value of the condo will decrease overtime and your thoughts about the situation.

But like any investment opportunity you also have your challenges and risks, high rental vacancy rate in the wider Fort Myers area suggests potential difficulty in securing tenants and consistent rental income. 

it is only as good as its sources and has difficulty determining the quality of its sources.  

The main difficulty is that the scale of money for this property just isn't very high.

lets face it you probably made and investment you did not understand or should not have done if your having financial difficulty because your interest stopped..