It's all going to come down to evaluating needed upgrades & repairs ROI - for every dollar you spend, will you get that back in a higher price or quicker sale?

We represent many carriers and we have been seeing them get more strict on guidelines and them become quicker to cancel/non-renew policies.  

I continued my program of over paying the principal amount of my monthly PITI to bring the loan principal amount down quicker as well.

Conventional loans will follow the same guidelines, here is a good excerpt:https://selling-guide.fanniemae.com/sel/b2-1.3-03/cash-out-r...DSCR loans have flexible seasoning, which could allow you to put the money to use quicker, outweighing some negatives.

I learned how to do finish carpentry, but a professional finish carpenter can do it quicker and better than me.Doing this to save money is usually the wrong reason.

But if you look at other global macro trends you see other things forming quicker and I won't get into that, but that doesn't mean this isn't coming.I'm very tempted for the first time ever to sit 100% cash and watch, I may do this as we enter first business week of June.

That way if you sell the place quicker than you anticipated you can pay the loan off without any financial  consequences. 

Please see below an edited version of the message that I likely tried to send you:Hi Future STR Mastermind Member,I am copying and pasting this message to everyone because I can’t figure out how to group message in BP and thought this would be quicker.

Likely to get quicker gain, but without experience and low money down, your risk will shoot up exponentially.

You can't count on believing that the family member will not produce a handwritten lease (real or not), or other paperwork & tactics, to throw a big old wrench in your initial/expected timeline.You CAN expect that if they see you as the big old rich/developer/bad guy enemy, they will do as much damage as they can, and drag their feet as long as possible.See if you can feel out what the relative actually wants/ needs, connect/come prepared with info on resources for local "housing help" options, etc (perhaps), and figure out what you can do to solve the problem (cash for keys with an incentive for quicker move out timeframe?