I’ve saved about 50k and ready to invest into real estate.

I think the market is getting close to being at the top, could be another year or two but the savings bypassing capital gains I believe will supersede the appreciation gain.   

The area is not the worst or best, but someone could save money over the hotels in the area and have some privacy to boot. 

But they don't break the bank when compared to the taxes saved by being able to put exchange dollars to the improvements.

It might mean you lose the deal, but it might also save you if something terrible lurks. 

I could also pay more monthly cash out of pocket as my finances allow it but I'd prefer create cash-flow and put that extra cash into other savings or investments.Any other pros and cons of shorter vs. longer term HELOANs?

You don't need to get a license to work on your own properties and if you are just using it to "save money" on RE transactions, its probably not worth it.  

My sister wants to get involved and will be helping by assisting me in whatever reno projects we can do ourselves (probably just painting, tiling, flooring, and basic stuff to save on labor) and by letting me use her good credit for finance options.

I'm using one of their recommended hard money lenders since I wasn't up to that level of savings yet, so taking out about 150k at 12% and 3 pts. 

Every time I search NWI (northwest Indiana) I don’t see much, save for a couple of threads now years old.