By the way, we prefer to go through the reimbursement route instead of taking a deduction on Schedule E -- based on what I have researched, we would actually get more money, and it's cleaner and hopefully would rouse less suspicion from IRS examiners.4.

If you are not out I need to reschedule cleaners, possibly painters ....  

Gas is cleaner than oil so your utilities won't need to be serviced as frequently, saving you money.Cost: New electric baseboards I have heard are now more efficient.

However, if that wasn't an option I would ask my realtor for a recommendation for a cleaner and handyman and pay them to get the property set up. 

Need to have reliable cleaners and a handyman.

A motel has full staff, cleaners, daily tasks, whereas your four-plex has on-call management.

Again if they are handling the cleaner that is their expense not your expense.  

If you do come across a unicorn multi that isn't a complete gut most house hackers run into the issue with the standard of living for their investment property and their own house are drastically different.I would suggest looking out in Delaware county for a multi, much higher inventory 3+ units, and a larger percentage of cleaner multis as well. 

Here is a very simplified example of what I mean:Option 1: Single property Gross 100K net 30k Option 2: Two properties: Gross 100K net 40K Now, of course you you net more on option 2 but now you need to manage double the bills, double the bookings, double maintenance, cleaners etc...

I have heard and read many posts about how reliable cleaners are essential for STR business.