It’s awesome to see similar minded people around the area!

@Tiffany Da Silva, I use quickbooks online for bookkeeping and I use a "Profit First" approach to managing cash.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

But in my mind that's your best case scenario, take your profit at the beginning, maybe buy a couple of the houses at a discount on the back end as rentals if it works out, but for sure I wouldn't want my profits for improving raw land tied to the final sale of the home unless I was incentivized to do so.  

thanks john. would you mind sharing your excel template? 

You have to start with your long term goal in mind.

Management has to allow you to STR, and not change their minds in the future.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

If you're asking about loss harvesting with real estate as the asset, you can typically only loss harvest when you sell an asset, unless you sell that property and it has a loss, keeping in mind depreciation, you won't be able to loss harvest.

It's kind of the off season for rentals, so I would take that in mind also.