Eventually, Class A property values increased to the point that even increasing rents didn't allow them to cashflow upon purchase.So, the flood of new investors switched to buying Class B properties.

Take a look at the HOA and see if it changes every year, HOA price increases can factor in on your profits with respect to Condos

Hey Felicia,If you have a genuine reason (increase in family size, relocation, etc.) for a new primary, then an FHA loan could actually be an option. 

I am sorry, but I would run from that syndicatorIt sounds like you lost $13,000 from this investment or at least this property calculated as follows($50,000) + $5,000 + $32,000 = $13,000On top of that, he may have increased your overall tax burden by doing a cost segregation in year 1...

However, landlords must ensure that their late fee provisions are "reasonable" and do not violate the state's usury laws, which prohibit excessive interest rates and charges.Under Maryland law, commercial landlords are required to give tenants at least 45 days' notice before increasing rent or changing other lease terms, including late fees.

I recommend staying engaged with the forums and podcasts to keep learning from others' experiences.Given your success in short-term rentals, consider focusing on that niche initially.

For example, could this potentially be a cash boom opportunity within the adjacent areas such as Kenosha and Mount Pleasant where one could buy low, sell high within a relatively short amount of time through appreciation, or would the presence of Microsoft increase cash flow in those areas?

The seller dug out the basement to increase the ceiling height which required  underpinning.

These types of properties are easier to come by, often better priced, and can increase your overall rent for the property. 

Quote from @Michael Chalke: Unfortunately, Section 8 increases must be approved by HUD.