Be careful of SVDP.

But unless they advertise the seller finance (and be careful as most are really bad deals), then you'll need to talk them into it.

I say, if everyone is talking about it, it's probably too late.Be careful not to reject someone's advice in a city you haven't heard of much.

If the covenant specifically prohibits renting out rooms or STRs, you may be restricted from doing so.You should carefully review the covenants tied to your property to understand the specific restrictions.

Instead of lawn care, you have snow removal. 

If they find out, they can get really intrusive and they do not care about your circumstance.

Doing a conventional loan for each property is out of the question due to my debt-to-income ratio. 

1) If you continue waiting for the "right time ”, you’ll always be waiting.2) Your current job doesn't care about you.

One thing I did note is my insurance is $3K a year lower due to the monitored fire suppression system in these larger properties versus my smaller properties that sleep 12 or less built close to the same time.As someone who has lived in Illinois twice, the politicians there don't care if people burn as long as they can tax and spend. 

That's missing the forest for the trees, but you do need to manage cash flow because if you're buying conventional you'll come across DTI issues soon and if you're buying nonQM it needs to be 1:1 ratio at minimum to be qualified without unfavorable terms.