They will appreciate the drive up access, versus elevator/cart system. 

Best return on investment for single family homes is kitchen remodel, adding a bedroom, adding a bathroom, curb appeal (front landscaping and front home elevation, painting in and out.Check your local codes and ensure you use permits to add any bedrooms or bathrooms (or square footage) as it will not go onto title without the permit.

People didn't like elevators, closed amenities and who needed to be close to commuting routes?)

The following items are covered under building coverage as long as they are connected to a power source and/or installed in their functioning location:Sump pumpsWell water tanks and pumps, cisterns and the water in themOil tanks and the oil in them, natural gas tanks and the gas in themPumps and/or tanks used in conjunction with solar energyFurnaces, hot water heaters, air conditioners and heat pumpsElectrical junction and circuit breaker boxes and required utility connectionsFoundation elementsStairways, staircases, elevators and dumbwaitersUnpainted dry wall and ceilings, including fiberglass insulationCleanupThe following items are covered under contents coverage:Clothes washers and dryersFood freezers and the food in themFlood insurance does not cover basement improvements or items not necessary to make the home safe, sanitary and functional -- such as carpeting, finished walls, paint, floors, ceilings, furniture or personal belongings that may be kept in the basement.

labor/Material rough estimateFlooring(labor) : 2500Flooring Material: 1.5 per sq feet + paddingKitchen - 3000Cabinet & counter top ( see/select home depot website)Bathroom - 3000Tile + Tub and fixtures ( see/select home depot website )Electric - 1500 ( inside unit )Electric Materials ( see/select home depot websitePlumbing - 1500 ( inside unit kitchen and bathrooms )Plumbing Supplies see/select home depot websitePainting - 3000Paint see/select home depot websiteWindows ( replacements ) per window $450 all includedCleaning - $350 final cleaning Trash Out -$500 ( includes dumpster and dumping fee )Appliances - 2000// Total (without materials): 18’700 From Inspection Report Labor ONLY 3.3 - Repair gutters - $475 5.4 - Exhaustive fan (kitchen) - $3505.7 - Dishwasher - replace ( $450 )9.3 - water heater - fixed and fixed all the leaky gas lines - 2K10.7 - replace all outlets - $25002.9 - Insulation not present (basement) - 4.1 Damaged drywall (wallboard contractor) - $ 7504.2 - Wall - elevated moisture leaking window - replace window ?

However, now prices are so elevated and affordability is so poor that it now seems even more likely that there will be a pullback.

I know that the purely safe play would be to buy in some out-of-state market, but like I said this is a property in which I have interest and I'm trying to gauge whether it's a reasonable risk to take.So what I want to ask here is: what kind of questions do people here ask themselves when considering deals that have elevated risk like this.

Since I know exactly who will have a permit or not (which will likely not be a handicap person because there is no elevator) why can I not rent those two spots out?

I sent my elevator pitch as a message response while attempting to connect with local investors.

I do like the idea of a refi if rates go back down, although I've been told a lot of investors only hold the STNL properties for 4 - 7 years max before flipping, since the risk elevates and the value drops as the lease term draw downs.