But for the condition it was in and what it needs vs. price they wanted and my own circumstances,  not the best move for me.

In your circumstance (congrats btw), if you wait too long to cash out your available equity, that equity could go south just like the investment properties that you're hoping will be cheaper by the time you buy.ie. 

There are so many unforeseen variables that will impact where rates are in the future.

@Mike Trzaska inbound marketing is king under any circumstances...that said, I do believe direct mail has a place... and your approach to writing handwritten cards will yield the best results.

The tenant must make a rent payment as close to the actual rent as their circumstances allow.  

There are only a few circumstances where a cash offer is more beneficial to a seller.

In terms of cash reserves for unforeseen issues I was factoring in a 10% buffer into my 30k.

@Kimberly Carver In normal circumstances it would be easy to evict a holdover tenant because it's easy to prove the tenant is not a legal tenant when the lease is active there is a burden to prove the tenant has materially broken the lease.  

I think you'd do well in our area given your current circumstance.

Valuing a property is very subjective and you have to take the totality of circumstances into account.Good luck!