Then the time cycles usually come into play. 

You have come out with a narrative that is the exact opposite of the collective experiences of 1,000's of investors and PM's who've collectively dealt with 10's of 1,000's of Section 8 tenants and are refusing to provide any insight into your experiences.

Quote from @Ben Scott: Make sure to close the transaction at a title company and have the deed and title put into your name.

I looked into an umbrella policy in the past, but the ones I found would only cover the amount over what the original insurance policy would pay.

You want to break down your preference in regard to sale price, down payment, program, (SFR/MFH), seasoning is important, and the two R's you want to pay most attention to is the Renovate and Refinance.Most investors make the mistake on the renovate or refinance and sometimes both.You also have to figure out if your buying as a Primary or investment because if you buy as a primary you always refinance before you rent. 

You'll have difficulty selling it and breaking even with disclosed leaks.OPTION 1hold on with long term rental strategyOPTION 2Increase your revenue with 1 furnished MTR for the medical groups. 

What advice would you give to someone aspiring to enter into Real Estate?

An egress roof window would get you into the roof which could get you over to the second floor stairs, I'd have to add a few more stairs but that would be easy. 

Generally speaking, I have not seen underwriters look too deep into occupancy concerns related to second home vs investment property since Fannie/Freddie installed new LLPAs a couple years ago that make the pricing for each aligned in most cases.

Sending quality information/updates through email to the people who contacted you and opted in to your email list could lead to similar results - IF you don’t bombard them with continuous sales pitches and or irrelevant information.