I'm in Phoenix, where it's brutally hot in summer and a lot of houses have pools. 

Personally, I would look to buy that kind of property and house hack it - meaning you live in one unit and rent the other 3-4 units out.

I also thought about buying two houses in the same deal, but my long term broker (the 30% broker) who said they can not do that. 

I have been doing TurboTax for last 20 years and some of my real estate i purchased were in 2009(condo) and 2013(townhome) timeframeSince you purchased your properties in 2009, you likely purchased the properties at a lower price point than what the houses would sell for now.This means that your depreciation would be lower than others who purchase homes now.You should still have a benefit by depreciating the homes.

We are headed out to Bremerton this weekend to see the house we are purchasing in person.

Even "turn key" rent ready houses will have some expenses.

So i am a 23 year old who has worked his butt off since 2020, i currently have 20k saved for a down payment and by the end of the year i hope to have a maxed out emergency fund maxed out and potentially 30k for my house fund.

All my houses currently have good tenants that pay on time.

Lessons learned: 1) Do a more thorough tour of house before purchasing 2) Have more money saved Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I was researching a house I owned built in 1939 and it took me three visits before they found the file.