@Nick KatsikisThe source is the Temporary Regs to Section 469 of the Internal Revenue Code.

That sounds strange, but you have nothing holding you back from venturing out of your security...because you have lost that security blanket that was your job.I would venture to say, that most of the success stories in history, started out where you are right now...me included.So, with nothing holding you back, and with plenty of time on your hands (time will always be your greatest asset...since you can never get it back), if you want to get into REI, you need to do the following:1 - Learn,2 - Learn some more,3 - Keep learning.Places to learn (before you say "that costs money"), that don't cost any money are:1 - Online education sites that have free articles written by experts in their fields.2 - Free e-books, that you can get online.3 - Joining your local REIC's to both learn and network.4 - ...and never stop learning...even when you become a success at this (and you will)Also, three very critical actions you MUST follow to be a success:1 - Always think possitive.2 - Train yourself to think of future "obstacles" as temporary problems...and you are the problem solver. 

Depending on your situation and the condition of the roof, I would recommend either a temporary repair to solve your immediate need, or a complete re-roof.  

If you are looking for high level analysis you probably won't find it in a forum post, you might look on Upwork.com and see if you can find someone who specializes in the area of analysis you are interested in and is willing to take on a temporary side job for a fee.

That is my big question on this whole deal, what has caused him not to make payments, and is it temporary or permanent???

My question is- am I better off continuing to save and buy something bigger/better later down the road OR do I jump into this as a temporary primary residence and future long term rental? 

I think most of the independent, smaller landlords operating in C/C- areas are probably a bit more willing to work with tenants having temporary problems to avoid evictions and skips and as a result may have lower eviction rates.

But I'll be coming down to Mobile, AL in the next month for a few temporary duties and plan on touring properties while I'm in town.

You have a temporary problem getting the financing you need as an owner occupied home.

AirBnb has been something I've thought about but just not sure since it's temporary.