Tenant has been there for over 20 years so the unit has a ton of updating that it needs so that the unit is brought back to life. 

If you have a $500,000 2.5% 1st mgt and want $50k you'd be insane to choose Cashout over HELOC.

However, there are ways to structure your 1031 to accommodate virtually any timeline you can think of -- sell one, buy one, sell the other two...buy, then sell all three over time, etc. 

This is called reverse amortizing b/c rather than paying down your loan the loan increases over time. 

My #1 tip would be to not over analyze things and just get going on a good deals.

People often have their closest friends over to their place often, far more than say, 7 times a year.

If so looking for opinions on software, which ones you vetted and why you chose one over the otherThanks

I've been pondering land flipping for over a year now and think maybe now is the time to dive in, head first!

They have purchased over 150 STRs and they are very knowledgeable and data driven. https://www.strsearch.com/

@Andrew Galloway The STR market is very competitive here with over 40k units.