Brand new and looking for advice ! MA and NH area

[Cameran Binette]

Hi all, I've been recommended to come to this site for some information and advice. 

I wrote this whole thing and realized i never wrote a intro post.

I'm Cameran, im 26. 
I do not own any properties 

My goals and reason for coming to this site is to provide my father with a place to live through retirement and build myself a income from rental properties. 

Following is why I'm here- i apologize ahead of time if this is in the wrong place. 

Right now I live with my father, who is 61 and is getting old. He has done contracting his whole life ( siding/windows/bathrooms/roofing etc for 40 years ) . He has nothing saved for retirement . No pension, no 401k, no IRA , no secret stash under the bed . Zero. He had mentioned selling me his house while hinting at him being able to stay here. Well I don't want to have my father live with me the rest of my life but I refuse to not find a way to help him.

Right now he owes 110k on this house, which is worth roughly 300k. If I were to buy this house at what he owes, I would have about 200k in equity right off the bat. But why would he do that that seems dumb right ? Well he's getting old and wont be able to work like he used to and will be living off what little SS he gets and he'll probably have to get a part time job. That's were I think I can benefit him and myself greatly. 

If I use that equity for a down payment on a multi-family property , a tri or quadplex. In theory I could put him in that house at no cost to him and with the right deal still make money. He benefits from having a place to live for the rest of his life without having to pay for housing. What id ask of him is to take care of the property - cut grass, paint or whatever task may come up, until he gets to old for that obviously.  

I do understand I would have to wait before trying to take out equity in the house but this already a lot,  so explaining timelines as well is just another added confusion. I'm going with 1 property per year giving a full 12 months between trying to apply for loans/lines of credit etc. So buy this house, wait a year for the one for my father. But with that being said I should have enough equity in the house to purchase another multi family property for cashflow, with the intent to continue the trend of buying properties. 

I know I definitely need an accounted, lawyer and real estate agent .

My biggest hurtle of all of this is going to be convincing my father that this will work. In theory I know it can work.   He's doesn't like the idea of dealing with tenants or people, not that he would be he'll be afraid this will fail because of something out of our control. I'm not scared, i'm willing to make this work because frankly I don't want to be him in 40 years. 

 I'm looking for some people who may have done something similar or owns property that could show me the numbers of how it works so I can show him when I approach him about this whole thing that it can work. Also if anyone has advice , I'd glady take that too.

Thank you very much if you took the time to read this whole thing, I appreciate it . 

-Cam