You can expect to pay about $5k per year or so, depending on where your unit is and how much you pay for it.I can give you more accurate details and help run numbers on your unit with you, if you like.

Depending on where you are looking, inventory for 1-4 units can be a challenge as a lot of the NW suburbs are all single family homes unless you are further NW like Rockford or Elgin or something like that. 

Just depends on your experience level and the network you have.

Costs may disqualify the opportunity even though in theory it can be converted.I believe its important to set expectations and if this is an 8 bedroom RSA5 home just as an example you very well could be looking at a building that's obsolete and again even if it is RM1, depending on the costs of the conversion, still potentially obsolete.

Congrats on at least taking action.You've got nothing budgeted for vacancy that I can see; it depends on how much turnover there is in your market and what your prices are like compared to the rest of the market, but most people would budget 1 month of vacancy/year/unit.

Depending on how many properties you have that may be overkill.

These losses depend on the layout and geometry of the system (ductwork, piping, etc) and the insulation used, the ambient temperature that these ducts/pipes are traveling through, the temperature of the air or water/glycol mix etc...  

And yes, sometimes you have to pivot depending on other parts of your portfolio.The issue is that a flip is higher end finishes and amenities than a long-term rental so you could overdo the market if you have to rent it and get less of a return for the finishes.

For example, for rental properties, lots of the categorization depends on the REI's specific tax strategy regarding what we're capitalizing versus what we're immediately deducting.

@Ian McClureI would say it depends on the tenant and what they are needy about.