Most of the time there is a ton of deferred maintenance, bad tenants, turnover, etc., being the reasons many landlords want out.  

Hi @Drew Pak, if you're an accredited investor, decide to sell and want to defer your capital gains tax you might consider reinvestment into DSTs (Delaware Statutory Trusts).

This is with a baseline of cash set aside for each property to make sure I am prepared for repairs and capex.Put more succinctly, when I look at the 401k I see 3 options:Keep it in 401k/IRA, in stocksUnpredictable return, with little real controlKeep tax deferred benefitsCannot use without penalty for 30 yearsRoll over to SDIRAMore control over return, more stable instruments are availableKeep tax deferred benefitsFairly limited on vehicles that I can use due to leverage being (in my analysis) untenableCannot use without penalty for 30 yearsCash out, invest in cash-flowing rentalsMore control over return, more stable instrumentTake a big tax / penalty hit nowTaxed on gains each yearMost flexibility on what vehicles I can invest inCan build rental portfolio more quickly (more to begin with, plus quicker path to use proceeds for new properties)Can access these funds for "retirement" without relying on an arbitrary legal ageI can show some more detailed numbers if you think it'll be helpful, but even if you take my analysis at face value, I'd love thoughts on the options I'm considering.

I took that equity in one San Diego little condo and traded it in for massive cash flow and using the Apartment complex business model have a property manager due all the heavy lifting and have become financially free, with $120,000 tax deferred cash flow per year, while forcing appreciation on 6 Apartment complexes and going from 10 rental properties in San Diego to now 87 front doors and counting.  

:grin:It's about keeping up with the issues and I did that w/o going to deferred maintenance.

Could I buy my parents house under an LLC for say $5000 and keep it as an asset deferring the capital gains tax into another property?

A property with decades of deferred maintenance. 

I like that you are forward looking on planned projects, reserves, and deferred maintenance, if any.Having just wrapped up my Schedule E, I see my dues from a 2002 condo purchase  (once a nice "on paper" cash flow property) is now the largest expense by far, eclipsing mortgage interest etc. 

I will start working through this information, and I'm​ looking for more suggestions.I have an appointment with a CPA at the end of the month and want to be ready for that conversation. since they are busy with tax season right now, I figure this forum is a good place to educate myself before the chat with the CPA.Already, I learned about a Solo 401k which allows me to put up to $53,000 into tax deferred retirement savings.

There can be a huge difference if you have to evict someone, turnover costs are higher than with higher quality tenants, the home might have deferred maintenance, and the list goes on and on.