Leverage and the ability to control larger assets also produces the ability to amortize larger loans over time.  

There are issues with it, but don't go OCD over a logo as it will not enhance your ability to find or close a REI deal.

The problem is...We haven't been able to save in huge chunks and it has left us without the ability to make a 20% downpayment on anything, especially given that New Haven is an expensive area.

I could seriously consider transitioning my life towards something more entrepreneurial like this down the line but only when I feel super confident in my ability to parse it, live the language, and strike a balance with my wife as a team in the process.

Reviewing existing leases (i.e. learning your ability to kick out the family members and get in market rate tenants) and the rent roll should be part of your due diligence.

If your point of flips being safer were true, then wouldn't banks (who make money on their ability to evaluate risk and judge interest rates as compensation for risk) rather lend to flips versus rentals?

I've approached companies I work with and told them upfront that I want to advance to the MF sphere from the SFR properties and need some past done deals from them in order to soak them in and learn about it. i found this approach to work well, and I don't think developers/agents would say no becasue this will give u the option to trust them and work with them for your future purchase, hence - eliminating the lookie-loo position.that being said, i would also love more references for past deals in order to optimize my ability to analyze the deals

An S Corp is extremely limited in its ability to create different types of equity ownership interests.

This will not have any major impact on your ability to setup and contribute to a Solo 401k plan.

Or find a way to put it back on the tenants for not informing you about the leak and ability to address the issue.