Can you handle extra debt with your current income?

I personally would like to continue buying properties to rent out every year but he feels that is risky and will lead to unpayable debt.

Foremost, do thoroughly check out the current situation regarding legality/licensing/hotel occupancy taxes for short term rentals in the city/area.

They are great for short term debt that you will pay back quickly.If there isn't a solid plan to pay it back quickly, cash out refi usually makes the most sense. 

Hello BP, I have a question regarding hard money loans and the debt-to-income ratio. 

How can they not cash flow if they have no debt?

Assuming dad has at least acquiesced to the sons' occupying, they may legally be his "guests" not his tenants. 

Caveat- I have not specifically looked into this and this is not intended to be relied upon as legal advice.The best person to ask would be the county prosecutor in charge of environmental issues, or someone at the county board of health. 

Again I have a low paying job and live in a high priced area... so thats why I'm hoping to go this route than a hard money lender.If all of this goes as planned and I flip enough properties for a profit, all of my proceeds will be put into a savings account and used to buy an apartment complex at some point in the future.So thats pretty much it, before all this I thought about doing wholesaling but know its harder to get sellers to sign their homes to you and I've never been a good salesman either, let alone any potential legal issues with it... so I don't think that's the right path for me.Any input would be GREATLY appreciated!!

If this death does not specifically trigger something (such as acceleration of the debt), then the agreement as written continues to be enforceable by the decedent‘s estate or heirs.