I don't need a broker to write a contract but I do need one to get into any properties that look promising.

I see many write that you can buy a multi-family, live in it for a year and purchase another multi-family.I can see going from a multi-unit house to single family house but can’t see taking advantage of the second tier entitlement from single to multi family, I know va loan officers and underwriters can be sticklers due to the va loan guidelines, so my question is to any former underwriters/loan officers, what are considered some legit reasons to take advantage of the second tier entitlement and what tangible evidence needs to be provided?

For example, none of the local lenders I use in the area charge a lender's fee for writing the loan, which could save you thousands! 

If you are not a licensed entity without a managing broker you cannot: write ads of properties (owners must write ads), you cannot negotiate leases terms with the applicant, you cannot collect rent in office (regardless of whether it is made out to landlord), you cannot operate a trust account, and finally you cannot enter into contracts for services (i.e. hire a plumber, lawn service, trash company) on behalf of the landlord. 

Don't know how much as the writing on his sign is too tiny, but the unit next to him sold for $475k.  

Because of where we are in the cycle, I'll typically write my offerings with a ten year hold, but the strategy of "buy, reposition, and watch for the optimal exit" does not change.

Your CPA  is correct - here in the US we do not write up any appreciation of our assets. 

All maintenance is done by tenant, if not just write it in your lease. land leases in my area are 200-275 per acre.

If so then all adults must be on the lease which means you need to do an addendum to the lease or write a new lease. 

Assuming you own them under your own name, your accounting should be the same thing - the only difference being they are going to be reported directly on your return as opposed to doing a return for an llc and then having the bottom line number (i.e. profit or loss) flow through to your personal return.You can write off depreciation, mortgage interest, property taxes, repairs, etc.