Assuming they are professional and skilled in the craft - alot of the issues you have faced, they will remediate and mitigate moving forward.

You’ll put 5% down but get 2% back on sale (which might pay for your closing costs) and then do a rent by the room to cover your expenses and downpayment for next year) Not sure which university you are at but both Henrietta and South Wedge are solid places to start (serving RIT and UR respectively) Good luck, I personally think Rochester is a great area to start due to constrained supply with a growing population

No way does all the new supply subside by the end of this year.

My thoughts are current housing supply + high rates + high home prices in OR are restricting our options and liquidating the brokerage to pay off the townhouse = $400k asset + $2,400 cash flow that we could then use to leverage or save into buying another property outright or scale into 4 plex and use the rent to pay down that mortgage too.

Those are buyers not renters unless there is some other circumstance.I think you are right about supply....apartment construction is just about to come to a halt and unless interest rates drop in 1/2 probably won't see that pickup for a while. 

Consider cleaning, lawn care, snow removal and supplies as well as utilities  in your calculations.  

Manage their properties Provide welcome gifts/ goodie bags for their guests before check in Hauling extra supplies/ misc items to return to stores or other properties--Any other ideas that I can pitch to make myself more marketable?

. Install new hardware and replace any old drain and supply lines. Install niche and tile from bathtub to ceiling. Install new bathtub and GFCI outlet. Light and fan on same switch Install all necessary plumbingLiving Room Install sliding door board trim. Install spot lights. Install 3-way switches in the hallway, living area and staircase (where marked). Install new air vent covers.Hallway/Staircase Install 10-inch LED light. 3-way switch (one near kitchen other near bedroom) Place laminate with Metal bullnose Install spotlights over staircase and one at landing at the bottomo lights on 3 way switchesBalcony Paint railing. Replace lightBedrooms Install spotlights in bedroom (up to four per bedroom). Install new fan. Spackle, sand, and paint. Paint closets and shelving, ensuring proper installation of shelves. Install spotlight in walk-in closet.Outside Paint stair railing. Install or repair 2 doorbells. Install or repair 2 exterior lights.Materials Included Cement/hardy board, drywall material. Granite slab for countertop and bar. Kitchen sink (D shape). Setting materials (thinset, grout, drywall tape, red guard, etc.). Baseboards, door, and balcony trim. Plumbing materials (excluding fixtures). Fastener screws.Total labor cost: $13,000

Quote from @Andrea Lucarelli: I’m interested in beginning my REI career with purchasing a SFH or condo in Cleveland area (safe neighborhood) to list as a furnished rental for travel medical professionals, supply corporate housing needs, or house temporarily displaced families for insurance companies.  

But again I’m not supplying context.