Some say to never tell them and let a real estate agent show the house and what not, but I feel that I would have a hard time not being completely transparent with my roommate.

Feel free to hit me up and I can help with your financing.

My thinking is account for all expenses and hope that it being a new build will save me some time before having to perform cap ex style repairs (I do have about 50K cash on hand after the closing of this property so i feel comfortable with handling curve balls for a few years) New Build structure and neighborhood/school gives me hope that in 30 years i can still command a decent rent on a property 30 years old instead of trying to take something from 1970 all the way to 2055 and still get decent rent out of it .

I feel like maybe I'm asking for too much with this investment.

It’s not all about the Benjamins…………..A wise mentor once told me:The Benjamins are simply a concrete manifestation of the appreciation your clients and investors feel towards you.

I have seen that usually, in a dual agency situation, one party feels like they lost out somehow and it opens up the way too many opportunities for me as the agent to get sued.

Personally I think I don't want to deal with pets because a) it's a condo complex and I would feel bad for the neighbors if a dog was sitting in the unit barking all day while the family was at the beach, and b)  I live 900 miles away and would not be available to assess any potential damages incurred by someone's pet.  

Sure, my 401K (which has now been converted to an IRA due to employment change) will come back eventually but I'm not getting the benefit of the monthly rental income it it was invested in a rental property.I do realize that I may have periods where I won't have a tenant or will have to cover some property damage but I feel like I'd rather take that risk than watching my IRA lose 20% in a matter of months.BTW I use property management companies to handle my rentals.

Ask them how many units they manage, what they feel market rent for your property is, do the handle repairs in house or use contractors, what mark-up do they charge on repairs, etc. 

I saw a similar post about 7 months ago by "Mike Romano" with a similar question, however I didn't feel like he explained the reason why he was planning to use a HML instead of a standard conventional loan in the first place.