Over the recent years I converted it into a single-family home.

Going forward, make sure you convert your lease agreements to PDF and have them backed up.

Or the deductions for your business expenses like your cellphone, internet, tax prep, computer/tablet, etc etc. ) All rental real estate will eventually cash flow, bit coin never will  Here’s an easier test of what the “professional” money men think is riskier.

You weren’t trying to convert an owner occupant to rental. 

Purchase price: $170,000 Cash invested: $40,000 Converted a single family home into a short term rental What made you interested in investing in this type of deal?

As a senior baseball player looking to eventually play pro ball after this spring semester, I acquired a serious interest in doing real estate as another source of income.

You could also offer to cover part of their tax liability through negotiation or encourage them to convert the property into their primary residence to use the IRS exclusion for up to $250K/$500K in gains.

Even if they were to achieve this goal, they get demotivated with burnout and the eventual realization they aren’t working towards their goals, but away from them.Solution: First define your life goal.

Along the way I would love to get investors instead of lenders and eventually scale massively. 

However, since market shift / rate increase even these guys have slowed down quite a bit.Regarding regulation, I think eventually Indy will have to regulate against Short Term Rentals.