This smaller rehab would be repairing some couple foot by couple foot holes in the wall and ceiling, replacing several broken doors, refinishing the wood floors, putting new linoleum in the bathroom, putting in new cabinets (but keeping the sink) and painting everything.

I had purchased this condo 2 years ago and it looked like the Seller had just upgraded the bath & kitchen (including installing a new countertop & cabinets), at that time.4) If I’m allowed to deduct their deposit, do I just need a quote for this, or would we actually have to get the work done?

YMMV (your mileage may vary)Fixable alone: boiler maintenance and steam system rebalancing, minor lead paint sealing, plaster patching (even very large ones), thermostat installation, insulate flooring and rim joists, painting, floor repair, skim coating walls, installing thresholds, weatherproofing, installing/refinishing door and cabinet hardware, adjuster gutter drainageNeeded professionals: sewage main unclogging ($), knob and tube disconnection+removal ($$), flooring ($$), adding joists for structural support within walls ($$), replacement and removal of old brass/cast iron plumbing where necessary ($$$), new gas line for laundry and lines for appliances ($), wall demo + replacement ($$$), steam line moving and radiator repair ($$), gutters ($$)$ - hundreds, $$ - thousands, $$$ 5K-10K, $$$$ - tens of thousandsHope this helps, best of luck with the old home!

If you put your own short term needs ahead of your customers or clients long term needs that is not the way to build a solid and lasting strong foundation business for many decades to come.You want your customers and clients to win each time with their investments.

He works in customer service, he is not a professional painter.

I stuck to the modern theme - replacing light fixtures from Amazon, peel & stick flooring in the kitchen, and adding a fresh coat of paint on the cabinets and walls.

Before I was in RE investing I worked for The Walt Disney Company, and if I learned one thing, it's that customer service trumps all.

your inside track on nursing and nurses could give you a major leg up on designing and outfitting rental units with those clients and customers in mind.  

It might be worth reaching out to a few contractors as it might be cheaper and faster to go custom (sounds unlikely I know).

For someone with no RE experience and no experience managing rentals starting a property management company is not the first step if you want to win a customer's business.