What would tilt it "back in the favor of buying" is if we could at least come close to breaking even by renting it out.

New counter tops, some paint, fix a window, replace the tilt up garage door with a roll up, and some other minor tune ups. 

However in reading a few blogs it seems as though obtaining a clear tilte is a lenghty process.

Where operable windows are required or desired, casement/awning are your best design, followed by tilt-n-turn, then your single/double hung and, bringing up the rear, your horizontal slider.Finally, it also pays to "tune" your windows to your location and the exposure where they will be installed.  

Typically you are not deciding to use glass for thermal performance but for other reason like aesthetics. https://www.lowes.com/pd/SEVES-Glass-Block-Glass-Block-Common-8-in-H-x-8-in-W-x-4-in-D-Actual-7-75-in-H-x-7-75-in-W-x-3-875-in-D/1000095299This window is R-0 but I think the info is not provided here. https://www.lowes.com/pd/Project-Source-30001-Series-Tilting-Vinyl-Double-Pane-Double-Strength-Replacement-Basement-Hopper-Window-Rough-Opening-32-25-in-x-14-25-in-Actual-31-75-in-x-13-75-in/3683856This window is R-3.33   (U-value is reciprocal of the R-value)  1/0.3 = 3.33https://www.lowes.com/pd/ThermaStar-by-Pella-Vinyl-Double-Pane-Annealed-Replacement-Double-Hung-Window-Rough-Opening-27-75-in-x-45-75-in-Actual-27-5-in-x-45-5-in/3119077

My local group is tilted towards buy-and-hold single family, but there are plenty of wholesalers, agents, flippers, etc.

This may help tilt the overall value in your favor a bit.

Just a year before all this hit, they had refi'd their home for home improvements they were doing, it put them at 80% LTV, but when the market dropped, it lowered their LTV as well and they were upside down, so no lending agent wanted to work with them.The insanity factor was running full tilt.

In some localities, cases like these tilt in favor of the landlord.

Worst part: The floor in one of the units has a pretty good tilt in one room.