I used to be a realtor so I'm comfortable with the language but I sure would love to get some newbie adviceHELP!

And he's got a lot of expenses and write-offs.As for renting, we've plugged the numbers into Rent vs Buy calculators at Realtor and Trulia, and both say rent, for at least the next 15 years.We feel comfortable only paying $3K/month for either rent or mortgage.

None of us have; only you have and you have to be comfortable with all of it.

I'm more comfortable starting at homes selling in the $500k-$1m range and working up to the multi-million homes.

Looking at the housing shortage for those families in need, and looking at the housing voucher program I am looking for a property manager that is comfortable with the housing voucher system.   

If he uncovers any problem areas or something that he does not feel comfortable tackling I am going to go ahead and hire someone with a narrower focus.Again, thank you for the thoughtful answers, they played a role in this decision! 

I do not have my own taxes done by them (my guy does not want any new business...he's on his way to retirement) but those two firms are good at investment properties and I do feel comfortable recommending them.  

As an 18 year old just starting out in wholesaling, how could I build my credibility so sellers and buyers feel more comfortable and trust me when selling/ buying a home?

It sounds like at this point your options may be to either: A) see if there are other forms of investing he could get on board with and start there to see if he grows more comfortable with time and experience or B) table the investing for now in order to preserve your marriage. 

We don't have CPA yet and when we tried to consult couple of CPAs recommended to us, it was clear they have not dealt with investments and were not sure what to say, so we are not comfortable hiring them.Any clarification would be greatly appreciated!