If you pay two years' worth of property taxes in 2025 (January and December), both payments are deductible on your 2025 return, potentially reducing your taxable rental income significantly.

Quote from @Denise Lang: Hello everyone,my wife and I want to start our real estate investing journey to boost our wealth and retirement fund.

This allows for proper retirement of assets.If a property has already been sold it may still be a good candidate for cost segregation as long as you sold the building and have not filed the tax return.

Well, STR can work well for people who own a vacation house for personal use, and just want to generate some extra income when not in use.  

Most of us enjoy progress, we like to move the needle.I technically retired in 2015 from my W2 job on rental income.

Virtually everyone lives somewhere especially true for those that pay taxes (in CA property and income tax).  

All this just to hopefully cashflow a few hundred $$ a month, doesn't seem worth it.Lately, I am really leaning on just investing in REIT's like Realty Income (o). as I write this Realty Income is at $57.75 paying $0.264 monthly dividend.  

Did you achieve your income goal?

The South Florida will eventually be a retirement home and I got real lucky there so far.  

Then continue to scale - don't try and retire off one deal