Should I sell take profit and reinvest? or hold on to it longer?

[Michael C.]

 This is a very hard decision, I keep going back and fourth, I have a couple of rentals, one which cashflows pretty good 800 a month, that's with under market value rents, if I up it , I'm looking at 1,100 to 1,200 a month, easy to rent, literally there's people always trying to see if somebody moving out,  not much maintenance at all, the tenants tend to fix stuff before even calling me, Also these are long term tenants!  

 I lived in it 2 out of 5 years, so this is the last year to avoid capital gains,  my goal is to expand my rental business, if I sell I would walk away with 150 plus after everything, bought it for 180, if you include the downpayment and upgrades I did total would be 50gs invested!

Now I'm trying to figure out my next step,  yes I do have a plan with the money, going to reinvest it all into real estate and a little bit in crypto.. before crypto haters start to hate... I have been in crypto for years and made great money!

I'm curious on people opinions, Thanks

[Jake Wiley]

Personally, I have always tried to take advantage of the capital gains avoidance for the personal residence.  The caveat being that we've always bought properties that need a lot of work, and thus we build in a lot of equity through improvements and generate significant gains in a short period of time.      That doesn't mean that its the right move all the time.    

The way I see it is that we can generally do it again, flip the money into a new property, create value, avoid taxes and do it again.    Along the way, this also creates cash available for additional properties.  

In a market where there is high appreciation, it's possible the appreciation could offset the tax savings this year with appreciation next year.   

The question to answer is whether you could improve your cash flow by selling and reinvesting in more properties.