I had a terrible experience with full service property managers, I sleep much better self-managing but there are certain things I'm just not willing to travel for.

I'm amazed more people don't know about these companies, but I've been in your shoes before and it's a terrible feeling being outbid. 

.) - I'm least interested in FL because the areas I like have terrible flood predictions for 10 years down the line.

I accepted the tenants in place at a terrible rate.

If the asset can cash flow with the high rate and you are using the cash-out to purchase more cash flowing assets then I don't think it's a terrible move taking a loan now.

I always feel terrible about the cost associated with the formal application, but of course a necessary step in the screening process.

If I say that something terrible will happen - eventually I will be right.  

Some of it is good and much of it is terrible taught by folks who did two failed deals and now want to teach others how to become successful.

It is a terrible thing to be so far away and have a non-paying tenant.

Two things you may want to consider: $275k will not get you a multi anywhere here and if you do find one it will be in a terrible location or needing major work (not VA qualifying material).