"Gambling" that the value of the asset will increase also has its risks.

No way to make money on that deal if there is no equity and if it is underwater.If you could get it for $0 down with her carrying the mortgage, and it would cash flow well, it would still be a gamble to consider but the risk would still be on her. 

Kennedy Blvd & W 32nd St, Bayonne, NJ 07002$1,4502 bed1.0baOct 2017Average-priced listingHouse124 W 19th St, Bayonne, NJ 07002$1,3001,000 ft²2 bed1.0baOct 2017Average-priced listingApartmentW 4th St, Bayonne, NJ 07002$1,6352 bed2.0baSep 2017Higher-priced listingApartment42 Jfk Boulevard, Bayonne, NJ 07002$2,2721,022 ft²2 bed2/0baSep 2017Bldg TypeAddressPriceSizeBedsBathsLast List DateLower-priced listingApartment312 Danforth Ave, Jersey City, NJ 07305$1,100800 ft²2 bed1.0baMar 2018Average-priced listingApartmentVreeland Terrace & Garfield Ave, Jersey City, NJ 07305$1,6002 bed1.0baMar 2018Average-priced listingApartment70 Armstrong Ave, Jersey City, NJ 07305$1,2752 bed1.0baMar 2018Average-priced listingApartment130 Cator Ave, Jersey City, NJ 07305$1,5252 bed1.0baMar 2018Lower-priced listingApartment128 Neptune Ave, Jersey City, NJ 07305$1,0952 bed1.0baMar 2018Higher-priced listingCondo30 Constitution Way, Jersey City, NJ 07305$2,6501,250 ft²2 bed2.0baMar 2018Rentometer Listing IconApartment337 Ocean Avenue$1,075900 ft²2 bed1baMar 2018Higher-priced listingCondo15 Enterprise, CT, Jersey City, NJ 07305$2,7001,171 ft²2 bed2.0baFeb 2018Average-priced listingApartmentClerk St & Claremont Ave, Jersey City, NJ 07305$1,5002 bed1.0baFeb 2018Average-priced listingApartment264 Arlington Ave, Jersey City, NJ 07305$1,2502 bed1.0baFeb 2018Higher-priced listingCondo4 Constellation Pl, Jersey City, NJ 07305$2,6501,270 ft²2 bed2.0baFeb 2018Average-priced listingApartment86 Winfield Ave, Jersey City, NJ 07305$1,3502 bed1.0baJan 2018Average-priced listingApartment72 Van Nostrand Ave, Jersey City, NJ 07305$1,7502 bed2.0baJan 2018Lower-priced listingApartment137 Wilkinson Ave, Jersey City, NJ 07305$1,0502 bed1.0baJan 2018Higher-priced listingCondo40 Constitution Way, Jersey City, NJ 07305$2,7001,200 ft²2 bed2.0baJan 2018Average-priced listingDuplex46 Walnut St, Jersey City, NJ 07305$2,3001,298 ft²2 bed2.5baJan 2018Average-priced listingApartment16 Stegman St, Jersey City, NJ 07305$1,4002 bed1.0baDec 2017Average-priced listingCondo7 Tribeca Ave, Jersey City, NJ 07305$1,8502 bed1.0baDec 2017Average-priced listingHouseLinden, CT & Linden Ave, Jersey City, NJ 07305$1,5001,250 ft²2 bed1.0baDec 2017Average-priced listingHouse11 Linden, CT, Jersey City, NJ 07305$1,5001,250 ft²2 bed1.0baDec 2017Higher-priced listingCondo4 Constellation Pl, Jersey City, NJ 07305$2,9501,510 ft²2 bed2.0baDec 2017Average-priced listingCondo15 Cherry St, Jersey City, NJ 07305$1,9991,286 ft²2 bed2.5baNov 2017Average-priced listingHouseKennedy Blvd & Mc Adoo Ave, Jersey City, NJ 07305$1,5001,200 ft²2 bed2.0baNov 2017

If you really want to gamble your risks would be lower at the race track.

There are ways to break the corporate veil, but that depends on how you maintain your LLCs and operations and how strict or supportive of enterprises is your state.

Try walking into your bank and asking for a 30 year loan to buy some bitcoin lol.Personally feel like bitcoin is nothing more than gambling. 

It has been often suggested here and elsewhere to pursue something that keeps a toe in the water of the working world, as it limits the downside risks, and could turn into a fruitful enterprise for post-retirement.At the request of a friend and BP associate, I've been asked to provide expert opinion and electrical analysis on residential properties that are either on the market, or recently sold through his brokerage, as there are many customers who want a deeper look at their electrical system, deeper than what a typical home inspector will do, but they are not ready to ask a contractor to come out and simply give a blank check to 'fix whatever's wrong' (famous last words).

You can somewhat 'play' with that scenario by upping your appreciation input, but to me that is gambling if you push it too high. 

I currently have about 100k equity there.2016 capital gains income: 02016 business / gambling income: 25k2017 capital gains income: 152k2017 business / gambling income: 28kChecking account balance: 100k+Credit score: 730Investment property price range 165k - 200k.I can get letter from CPA stating I've been in the same business since 2010.I'm being told they will take either last three years of capital gains or last two years of gambling. 

With smaller towns there is always that gamble.