My 2 cents- the benefit is you get a cheap place to live with a very low money down loan and someone is helping pay your debt down.

And, since home values historically increase in value (4-5%) then I’m going to gain on that side as well. 

We also felt that the realtor  would roadblock us by not submitting offers that in their opinion was, "too low and the bank wouldn't take that" and was attempting to get us to pay for homes that we felt were too high, for their own personal gain on return. 

I’m a beginner investor looking to gain a wealth of knowledge and hopefully a mentor.

I'd stay away from asking people if you can shadow them for a day which benefits absolutely nobody because a lot of it would be responding to emails, making phone calls, pouring over spreadsheets and figuring the margin on a deal which to someone else who is new would not be the most exciting thing of all time.

Most are highly knowledgeable about real estate tax benefits and will work remotely with clients in all 50 states.

If you need all of it, you can sell and do a 1031 exchange into a new rental so that you don't get hit with capital gains taxes. 

i agree, i'm in the same place as you i.e if i buy a property the price can go down even 10% and it won't matter to me, that's true, but is there a downside to looking for an option that maximize the possible gain i can get?

(Also look into the FHA 203K loan)Another benefit to going with a multifamily is that it can "boost" your purchase price using 75% of the other income to help your debt to income ratio.

As long as you own or benefit from an asset, there will be some form of liability that attaches you to it.