However, you'll likely be able to put more money in your pocket if your reducing your living expenses in a HCOL area.

Partnering with your sister’s wholesale business or working in a real estate-related role can also give you valuable hands-on experience.

A 7/9 bedroom in a gated community zoned for STR is your best ROI for west Kissimmee.  

By all means give them a note on how to use all of the appliances (eg clean out the lint trap on the drier after each load, do not use dish soap in a dishwasher, change the furnace filter regularly, etc).

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

Once you know what is legal (seeing other listings in a particular area does not count as people do it in illegal areas all the time). 

This approach simplifies the sale and avoids unnecessary legal or tax complications.If she want to share the proceeds and tax obligation in a technical way, she need to file a partnership return for this property.This post does not create a CPA-Client relationship.

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

Ensure the sublease is explicitly permitted in a written agreement with your friend and aligns with local STR laws.

You can 1031 exchange it into multiple rental properties that will be positive cash flowing in a high appreciation real estate market.