I would be concerned with the roof, plumbing, and HVAC.

In the meantime, I'll start researching some architectural firms in the area - should I happen to need one ...

The property has 2 unites, around 1,600 sq ft and is going for $65k Apparently the roof is less then 7 years old but upon inspection it was discovered the roof has fire damage.

A new roof or ac unit may not be too obvious if snow covered when the appraiser comes out. 

Yes, a Buyer may want to confirm things by paying their own inspector, but if you can get an accurate picture of the roof, HVAC, plumbing, sewer, and electric, that eliminates 80% of the mechanical problems that cause Buyers to back out.

It's possible but you're going to need to be more specific on your goals and your current situation.

remodeled the units and roof What was the outcome?

If we expect to need $200k for our first deal, how much money should we target to raise?

COVID can have more social distancing implications and cause companies for office to need more space and less people allowed to work there.

Luckily, most of the work that needed to be done was cosmetic, but we budgeted for a new roof, new HVAC unit, exterior landscaping, along with interior cosmetics.