What is the best rental management software for someone with less than 10 units spread out between single family and small multifam?

Second home occupancy loans cannot be leased nor subject to a property management agreement.

If you need a good attorney, I can connect you with the one I use for our management side. 

I've already invested in a duplex in NJ (I'm renting it to two families and managing it) and a single family in MI (living in it).

I use Ziprent property management to find new tenants.

Take a look at some trade accounts and a line at the Big Blue and Big Orange if you are going to self manage.  

You're looking for increased cash flow, so managing more doors and/or strategically utilizing leverage can make a certain sense there...but as you mention financing costs aren't as rosy as they were 2-3 years ago. 

I'm structured and want to pursue something in real estate or money management.

They may feel a sense of entitlement, and they may not even be good renters.Unless this is some unique situation like a ranch that requires special skills to maintain the property, I recommend you remove the caretaker, spruce the place up, and put it on the market at market rates.I also recommend you look for a professional property manager that can help you navigate this immediately.

I have 2 boys and 2 girls.The girls are ideal money mangers and completely suited to managing properties and tenants whereas the guys are poor money managers and different very skill sets.