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?

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.

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

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.  

My family of 6 live and own in a ranch style 3br/2.5ba house with completed bonus room upstairs in a HOA neighboorhood.

However, in today's world, there's many ways to make a million in 24 months, and unless you come across a unicorn of a flip or you already have millions to play with, it won't come from RE.It depends on what you're going for.

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.”

I do wonder though how things would play out if large sums were involved.

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?  

I'm particularly passionate about building custom homes and using  the BRRRR method.Outside of real estate, I enjoy ATV riding, playing soccer and basketball and also traveling the world and connecting with new people.Excited to learn and connect with you all!