I'm guessing that your current employer covers insurance..

For purposes of the definition: • Gross receipts are reduced by returns and allowances made during the tax year, • An employee is considered full time if employed at least 30 hours per week for 20 or more calendar weeks in the tax year, and • All members of the same controlled group and all persons under common control generally are considered to be one person—see section 44(d)(2).

And the large complexes can actually be easier to manage because their size can often justify a dedicated maintenance person.    

You should look for current closed sales of condos in the neighborhood that are similar in size and age of the building, if it’s in the same building that’s the best.

Once split, confirm that the zoning is remains R2 (some cities have minimum lot sizes). 

@Jeff Wallace The position I held with my employer (while very lucrative) just didn't fit the lifestyle I had envisioned for my wife and I.

@Dawn YoungI took a self storage crash course and they recommend to purchase a property that is large enough to employ at least 1 full-time onsite employee.

This includes property type ( residential vs commercial), size ( range of units), location, age, price range (if applicable.) 

He pays what you call regular income tax PLUS 15% self-employment tax (Soc Security/Medicare).

It depends on your location, size of property, purchase price, nightly rate you can get, your upkeep of the property, and many other factors.If your unit shows well in photos and if you build up some good reviews in the first months, and your pricing is reasonable, it will be consistently rented.We have 3 of them, and all less than 1 year so the jury is still out, but in our experience so far, the startup and ongoing costs have been higher than expected, but all are getting good reviews, so in year 2 (now that they are stable) we expect to do pretty well.You have to make sure your town allows it, and you have to decide if you will manage it yourself and take on that extra work (communicating with the guests and people who will clean/make repairs) or if you will hire a property manager, which can be expensive, upwards of 25%.