It sounds like your trying to not pay long term capital gains taxes now and provide income in retirement. 

You'd likely be able to set about $10K aside.If you do not need the rest of the capital, you may just want to put it to work in rental real estate, which is pretty well situated as a tax shelter in and of itself.

Sometimes it can be hard to figure out why someone succeeds and another fails at it.97% of small businesses that fail, do.so because they are not properly capitalized.

I've done about 5 investment deals up to this point and have self funded each one, but in an effort to scale up I will need to look for other capital resources.

we've been asked the same question by a dozen or so good friends who live in/near SF about whether it's worth postponing the ownership dream, given where the bay area market is in 2018. personally, I think that right now is the time to hold off on entering the bay area market... unless you find a truly off-market, discounted opportunity through networking or a personal connections.sidenote: moving to the east bay (alameda, particularly) actually shortened my commute time into my day job in SF, compared to when i lived in SF. i'm sure you've heard this perspective before, but there's goodness to be found in the east bay, if you are dead set on buying in 2018/2019.from an investing perspective, there are still strong returns to be found outside of california. that's why we recommend to friends with capital that they consider looking into investment. that way they can start building wealth now and position themselves for buying that beautiful home when the time is financially right. sidenote: i recently posted on a similar topic on this thread. you can see if you scroll down and there are dozens of other helpful comments on this topic, on that thread: https://www.biggerpockets.com/forums/12/topics/587593-general-do-you-rent-or-own-the-home-you-currently-live-in?

You have put up 100% of the capital, you have 100% of the risk.

I have a tax/capital gains/ insurance settlement question:I bought a duplex 3.5 years ago with a conventional mortgage.

We lived in it from 2009-2015, and have been renting it out the past 2 1/2 years - so we won't have to pay capital gains tax on the sale - since we pass the 2/5 year test and the $500K exclusion test. 

Just got a question about what the capital gains tax rate is on selling investment property is these days?

Limiting your capital to purchase more deals.