I do not plan to sell this house within the next 5-10 years unless circumstances call for it so I am basically planning to buy and hold for the long run.I am hearing that all of this work could be well over $60K ($25K for garage, 20K+ for  3 high energy efficient HWH/Boiler combos, and $15K+ for roof)) which is causing me great concern.

I do not plan to sell this house within the next 5-10 years unless circumstances call for it so I am basically planning to buy and hold for the long run.

@Joel Owens - in a normal circumstance that might be the answer. 

Now you probably could get another loan to cover those but thats 2 loans now and probably a higher interest rate. i.e. hard money load which I advise against in this circumstance.

I never felt neglected.

You need to ask your local county tax office if a transfer fee/recording fee applies in your circumstances and, if so, how much you will have to pay.If your question is really asking whether there is an income tax consequence of transferring real property title between an individual and a corporate entify, or from a corporate entity to an individual, the answer is maybe.   

And nope a 1031 is not right in all circumstances. 

I'm confident it'd go for $1,650 under most circumstances, but I was not sure how much the school year starting would potentially delay renting it out.Even at $1,600, it'd still be above our initial projections and I'm anxious to get started on the next one once this ones finished up.

I could get about $300 a month positive cash flow, and I own the property free and clear in 17 years.So I guess the real question is, besides rare circumstances like this - what would be a reasonable reward, payment, etc. to make it beneficial for me to dig someone out of a hole and make it worth their while to trust me for the next 15 years.

The right realtor will be a resource for you, but under no circumstances should you be dependent on them.