However, I understand where you are coming from… I don’t usually partner on anything because.. why not just do the deal myself?  

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

There are also deals that can be find on jud.ct.gov for foreclosure auctions but those rarely work out because the people usually owe more than the property is worth or they get cancelled and postponed frequently. 

You'll want to have an insurance agent familiar with rentals since a lot of the extras on your coverage that you will want, the average insurance agent won't know to give you. 

-A water heater issue resulted in repeated mismanagement—confusing unit assignments—leading to extra costs to fix the same issue 3 times and on each occasion "more fixes" needed to the water heaters that I plumber said was needed.

If a person wants a different outcome, they usually do something different.

One of my early properties barely broke even, but after a couple of years, rent hikes and expense optimization turned it into a strong performer.For cash flow benchmarks, I usually aim for $200-$300 per unit, but your situation.. house hacking.. offers unique benefits like reduced living expenses and quicker equity buildup.

I like umbrella because there is no worry of being pierced for inadequate separation of finances, if sued you have a heavy weight in your corner who has all the consequences of a defeat, and because usually it is reasonably priced (mine today is not so reasonably priced but I believe it is mostly related to the risks of CA).I do understand that the probability of needing the umbrella policy is low.  

Just a few tips to look into but it usually takes some time to gain steam on your first listing so be patient and keep analyzing the local compeition /your own listing. 

Syndicators do this because most passive investors are not sophisticated enough to realize the "security" of the preferred return means they usually are giving up the potential for massive returns if the deal does well.This next comment would apply for all syndication.