I'm not a lawyer, and this issue could easily (more accurately) be resolved by a local attorney, but homestead laws are pretty wide reaching in that they prevent certain sales of property to protect the family.

@Theo Hicks Finding properties in the AO with the SOS is a great idea and this is something that can be easily outsourced to a virtual assistant that can be found on upwork.Jim---when you say mid-large size apartments...what range are you specifically looking for as far as $$$ and # of doors?

I recommend using a the HOLD spreadsheet: https://www.kellerink.com/resources/Easily lets you plug in the numbers and track cashflows and ROI.

If there's any questions about this, it is handled easily.

In some spots, I can afford it but January is a higher priced, very easily rented out time period and this person has requested a stay that leaves a single day on both sides empty. 

Airlines make you pay a fee for checked bags or a 6oz bottle of gut-rot wine or another 20% on your ticket price for a seat with 4" of extra leg room.

If that is a high-priority project and you feel strongly that it is the play you want to make, then I'd say today is a good day to go for it.If getting a property in our market is in the cards, you could easily accomplish that. 

If there are too many separate bills a tenant can easily pick and choose which is more important to pay when on a tight budget.

I can no longer easily terminate a tenant for things like too much clutter, too noisy, bringing unauthorized pets in but getting rid of them when notified, etc. 

I use this to easily have the data to give to my CPA.You can likely Google a good Excel template that you can use to customize as time goes on.I keep tenant info, AC filter sizes, trash pickup days, Magistrate info for potential evictions, Section login info in addition to the normal income and expense info.