I have no experience in renting to disabled tenants, and you eliminated my only wild hunch (Section 8), so I have nothing. 

If going this route, would the LLC structures eliminate the need for title insurance/any other insurance, since the only assets each subsidiary LLC will own is one property (or PA to the property)?

The attachments are usually paid at closing with the understanding the releases will be filed after you get your money.As an attorney collecting debt, I have had my attachment be missed and then gone after the new mortgage company and/or their title insurance and usually been paid as my lien is superior to their mortgage.

I want to take some cash and start investing in multifamily properties.It's a 2/2 Condo in a highly desirable location.Purchase Price: $97kOwe: $68kCash Flow (after debt service): +- $250/monthMarket Value - currently selling for +-$150kThe HOA is $450 a month, which is included in the rent price of $1550 a month, so it's not that big of a deal.So I'm trying to determine if it's more beneficial to sell it, take the cash and look for a duplex, or get a 2nd mortgage and take some cash out, since I'm so far in the green.Thank you in advance for all your input!

I have a lot of debt.  

When you've built a strong track record and are buying larger parks with higher values, agency debt will likely be the best non-recourse debt from a term perspective.

Taxes are just like mortgages, or any other debt....they get paid out of the seller's proceeds at closing, with a straight sale.  

Just be careful or just don't do it to eliminate this risk.As for the money with your parents, if they haven't said "yes you can borrow that when you need to replace the plumbing in two of your units", then I wouldn't count on it.

They will have to show the bank there is enough collateral with the remaining properties to cover the debt.

If you try hard enough you can find a lender who will work with you to get past debt-to-income issues and the number of properties financed.