I always thought I would do more of it, but I have only ever been involved in one deal with Subject 2 financing since debt has been so cheap for so long. 

But then, as short-term rentals became ever more popular, Americans tourists started thinking wait a second "We're paying so much for staying for a week at that short-term rental.

I am sure she is sending him letters (or using other methods to contact him) as well.I'm a small long-term buy-and-hold investor myself, but this property is about 4 hours away from my own market, and would be used personally by my wife and I if we were to acquire it.I'd really like some help from you large operators who work these deals all the time, as to how best make contact with the owner and see if he were interested in selling.  

I've always hated the term. 

I can take as long as I need to to fix the issue, especially if it breaks after being fixed.

As long as you do the accounting correctly, you account for it.

You should know the rules inside out or be working with the professionals that know it.Incorrect moves can result in not only a taxable event to you but to your investors.Based on your most recent response, i do not think you have a good understanding of1) requirements of the QOF(You may need to substantially improve a property)2) How long you need to hold a property before it can be sold to exclude the gain3) Inside basis vs outside basisBest of luck

Numbers in FL are not looking great with insurance/taxes/HOA fees/etc for cash flow but willing to  focus more on just breaking even (or close to even) and having significant long term appreciation.Option 2: take the cash, pay 20% long term capital gains and wait as market continues to dip for a prime buying opportunity.Would greatly appreciate insight/advice from those much more experienced and knowledgeable than myself.

If you were to rent it out long term, that's where you cross the line. 

I do wonder if this could be accomplished with a 7 residential unit and using one unit as a short term rental though.