I'm positive and hopeful they will work with me on this...My question is for you legal guys and gals out there: If I can't work something out with the Church, is there any chance at all I have a case for adverse possession here?

Zero chance of fraud issues.

I would start looking today, deals don't often pop up for your first time so if you think you'll be ready in Jan then chances are it'll take a few months after to actually get a deal.And finally something I did a little but not too excessively: reverse engineer. 

Taking on underfunded investment properties can become very stressful financially and emotionally.Remember - if you decide to wade in now "Cash Flow is king" meaning it needs to cash flow when you buy it don't bet on being able to significantly increase the rent to improve cash flow.Good Luck!   

HOA Express: they're currently in the middle of a redesign, which looks to be improving the dated UI they have now.

If we knew we could get her into one of the good charter schools (lottery system, so pure chance to get in I guess), we might just look at a simple SFH and stay there until we die or downsize later in life.

But $20K of upgrades might result in over-improving the property. 

I’m glad that you agreed to meet and given me a chance to get to know you and be part of your network. 

Andrew,The coverage for Vacant properties has improved over the past few years and the coverages available may not be a big drop off from standard coverage.  

But the way I see is I'm paying rent regardless, but wouldn't it be nice to have the chance to live for free?