Hopefully someone with tax accounting knowledge can jump in here with more detailed analysis, but I looked at this a bit several years ago...1) You still have to pay the depreciation recapture on the sale decreasing the net benefit of this approach due to the large tax payment in the 'sale' year2) The LLC would need to not be a passthrough entity so that it can be taxed separately from you, so you have to add another tax return cost for the years going ahead3) Taxing it separately from you likely means corporate status and corp. taxation rates which are higher than yours and I've heard many times over the years to avoid titling real property as a corp...Overall from what I've seen this only makes sense in a select few scenarios, which for most people aren't in play. 

Great start to life. 

I have said it before and I will say it again, my wife’s friend said it best when she said “The last time I trusted someone, I had twins.” 

We work with people in your shoes all the time. 

I had a mentor who stressed "you make your money when you buy"; the next place you get, be sure to haggle big time - and walk away if the price is not low enough.

Would love to hear from folks who've been through the process—what worked, what didn't, and what you'd do differently next time.

At this time I manage and renovate majority of all my units to keep cost low but most likely not the best use of my time although I'm skilled at it.

They equate the period leading up to the time its ready to rent as the risky part of the real estate process and pay a premium to bypass that part but this leaves them with unreasonable expectations because the real estate they purchase is inherently risky.

I'd sell because you are reaching the time when you lose the cap gains exemption and that $24K would take over 2 years of renting to get back.I had a condo that I owned for a long time and I sold it despite it being paid off and having long term tenants. 

I have a guy who has been here since July, but I renew his short term stay for two weeks at a time, every two weeks.