I had a job and recently lost it.

I understand that rents and flips will have different criteria's of renovations and that I could always get a contractor to go out and get a quote; however, is there a way to learn on my own and be able to analyze how much a rehab will cost just from walking a house and going to a showing. 

Can't speak to the organization in Michigan but generally the benefits of a well run STRA far outweigh the costs.I am a property manager in Hawaii so we are constantly being hit with new anti-STR legislation and have a large, well-funded hotel lobby to deal with constantly.

What would be the best use or strategy with a 75K HELOC to fund an investment property? 

Lots of good info here and at a good price too.

Home is 25 years old and requires a new furnace, A/C, and roof in the next 5 years. 

He's a good dude!

However, in general it sounds like a typical holdover tenant scenario.

I have no prior experience in real estate, however, am fortunately enough to have access to sources of income besides a fixed job salary that provides me additional CF and a long-term safety net.

Not your last big bill but a good learning moment