Good financial information and he explains how he started with house hacking. 

The house is 3,700 sq ft and currently listed at $108/sq ft, which is well below the $135–$155/sq ft range for other homes in the neighborhood.

Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

Hi @Leonard La Rocca III welcome to BPWith a goal to house hack your option will be much better and tremendously more favorable.1. $50k gets you the house but leaves you very little room for value add. 

@Ibrahim AtoumIf you're starting house hacking at 20, focus on building your knowledge and financial readiness.

Personally, I think house-hacking is the best way to start. 

I have a client house hacking in Hoboken who bought for a bit over $1.3m - they live in the top duplex 2/1.1 and rent the bottom duplex 2/1.1 as an MTR now and probably will make 4k/month.

Thank you I have presented a 40-60 offer to him now to see if we can get the house at the bottom dollar we would like I for but I am putting a lot of trust in him on the price and feel that we may be offering so low that I seller will not bite 

It's not likely you'll be able to rent rooms out for 1500-2K per month unless it is an extremely nice house/area.

Not planning on doing title insurance since we have owned the house for 50 years and we just did one at date of death.