In that format, the retirement plan could invest directly into real estate and there are no particular restrictions as to the timing of a deal.  

Those restrictions are lifted if you become a broker, but you typically need to work as a salesperson for three years before you can become a broker. 

Lately we received a email from the board member saying there is a restriction.

There are no restrictions on rentals from what I can tell and I called the HOA management company and the said the same thing.

It could be, in example, they restrict the building to no more than 5 units based on their density restrictions.  

Talk is cheap - look at his credentials before investing in a mentor.The problem with Washington investors coming to Baltimore - is that they pay too much because they compare DC prices with Baltimore values.Be smart about what you do and who you work with - you can look at listed real estate but your best deal is going to come from dealing directly with sellers.Also remember creative financing techniques - nothing down deals - Control and Roll System - Delayed Settlements - Hybrid offers - and don't forget owner assisted financing and make sure you always ask for a principal mortgage.Have fun - make full disclosures and make sure you understand the laws related to mortgage foreclosures - fail to do this and you may have a paid vacation to the Gray Bar Motel (a nice little room with one small window and the food is free, but the space is restricted).Remember your goal should be CASH FLOW or EQUITY - forget the emotional appeal - it is all about numbers - understand them and you'll do well in Charm City.Charles Parrish

Many communities (especially with HOA) will have restrictions and require approvals.

I'd be doing it myself but the NH laws restrict me from doing it in a multi family.

I just don't know where to start my research with the County with regards to other restrictions on the site and how to get utility taps.

@Emily Hobbs 1) Review deed restriction to see if they would allow it 2) If no issue , assuming parking requirements are met, typically you can build a second floor leaving first floor as garage . 3) If you have a very large property (20K SQFT +) or larger then possibly you can get away with duplex.