Sometimes it costs to play.

In Ohio and I wasn’t the one playing he ran off with my money.

He claimed that if we would just spend $2k on the backyard he would "increase the value of the house between 35-40%".I got him a $100 gift card to Armstrong garden just to play nice.

Why play with fire? 

In my opinion, some associations have way too much control and tend to take advantage of the out of state investors (not all of course).Is your preference to purchase another STR if a 1031 is the play?

@Tim Bender  Are you only pursuing deed's after tax sales where there is a redemption period in play? 

Again, this is like playing the lottery.

Huntsville AL definitely is an appreciation play right now;  there is no significant cash flow unless you put well over 20% down, go to C/D neighborhoods, do multifamily/house hack, or find a unicorn of an off-market deal.  

However, he starts to talk about how you may sometimes overpay for a property because you are not necessarily worried about what the property is worth today but about the “long-term play.”

All of that takes either time, cash, or both, and none of it is a pleasant experience for you or the tenant.During that time, would you have enough cash in your reserves to cover the mortgage for 3-6 months while the eviction process is playing out?