I was quoted an up front fee (~$2000) to retitle everything into the trust including eligible investment accounts in addition to my real estate and then a $500/yr maintenance fee (not sure what the purpose of this fee is).  

There are lots of options out there but expect to only be able to tap 65-70% of the equity and fees will be a bit higher than normal.

., landlord-friendly vs. tenant-friendly states)Everything is scored relative to the set of cities being compared, then stack-ranked.

Leases are legal contracts and the ramifications of poorly or vague language regarding late fees, early terminations, breaking the lease, re-let and the costs associated and "double dipping" in our state are very vague and there is statues that discuss "reasonableness' in accessing fees.  

As a lender myself, I was curious about their upfront fees.

Their MEDIAN rent figure is used for allotting Section 8 rents, but is useful for determining how your rent stacks up against the MEDIAN rent with is the rent where 50% are lower and 50% are higher. 

The HOA fees nearly doubled since then and now at $660.

Electrical systems will be mostly grounded and if you do need to update electrical it's possible you might need to only run a few extra lines or update your panel which is not tens of thousands of dollars but a couple of thousand dollars if some plumbing is older it could just be the lines going to your fixtures as opposed to replacing the entire stack.

I'm interested in knowing what options there are for alternative financing (stay away from $5,000 closing costs, ridiculous fees).

The quotes I'm getting for a DSCR loan via a broker seem super high... 7-8% rates, 1-2points, $1500 lender fees.