You do need 2 years for self employment, bonus commission (although commission not a issue if you change job with in same industry.

As an added bonus, there isn't nearly as much money chasing these smaller deals so they are often priced well (although they are rarely tenant owned homes so plan to divest the homes).

Any additional cashflow would just be a bonus. 

This is my my first property so im not playing the appreciation game, obviously that would be the bonus but Im shooting for living for free and covering most of my own utilities on that but i do include all of those expenses and cap ex and repairs when I do the numbers and came out of some cash flow.

That being said, if you’re buying an STR in tampa and going to self manage- you need to do a cost segregation study and bonus depreciate the property this year for a big tax write off.

Do they have any bonuses coming in over the next few months?

Ask for a scope of work to see what the $70,000 is for.Then determine what portion is eligible for depeciation over 27.5 years and what is eligible for immediate write off / bonus depreciation.Have a chat with a CPA if you are unsure.

1) ask your cpa2) you might be able to use bonus depreciation3) you’re really talking about a $3,000 deduction, so probably $600 in tax savings.

Royal Hawaiin air flew in there in Cessna 414s and in those days a passenger could hop up and fly right seat.. ( don't touch anything ) so I did that many times.. and as a bonus you might stop at Kalapaupa Leper colony to drop something off or pick someone up going to HNL. 

You're essentially getting $0 for those dates so any amount you can sell them for as an extension or earlier check in is bonus income.Let me know if you have any questions.