Generally, I would be tree trimming once a year to cut back any branches hanging over the houses because of potential damage, but also because of insect transfer.

I know that’s weird but we’ve been here for over a decade, know the market, and know there’s money to be made if we make the right deal. 

Quote from @Jim Miller: I hold a Florida real estate license.

I forgot. 

For instance my 90 lot subdivision at one point I had 90 legal descriptions and parcels on one master deed.. as I sold them off we just deeded them out separately.. its super common especially in older platted cities were lots might have been small like 25 X 100 and someone bought 3 of them and then built one home on all three.. some places they force merge them others you can go back and recreate the Old lots of record.. there is millions upon millions made by those that know how to find shadow plats and bring to life underlying parcels.

I have been blessed to purchase a home here which I have been house hacking for a year now.

I suggest starting with a  smaller single family property, and build from there.

I am on an H1B visa and new to rental properties.

I recommend finding a tax strategist who specializes in real estate taxation and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

welcome @Cam Caraher and congrats on joining BP, this place is the start for many, sure was for me longer ago than I care to admit.I'm not personally in your market, although was born in dorchester and grew up in NH, but this is a great place to meet locals.If you have not already a great starting point is the Meetups posted here, just search for your area and see if any meetups are happening.