If it's two mortgages, how common is it for a bank to do two at once for a new investor?

If there is a will there is a way.

Can you do a house hack?

I am finally ready to take a plunge on my first investment.

It is a duplex with 2/2. 

You've created a ton of equity.It's challenging to roll over the money with a 1031 into a syndication.

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. 

This is the part a lot of newer investors miss, but if you find a good neighborhood where very few properties trade then there won't be a market for you to find (or even know how to evaluate) a "good" deal. 

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?