I am a bit anxious about the kind of relationship I should foster with this tenant, and balancing the relationship between roommate and tenant?

Which is where you basically have a roommate or tenant renting out other unit to help pay for mortgage.

Tenant roommates covered mortgage and other expenses.

Tenant roommates covered mortgage and other expenses.

I would treat these two like roommates, since they have no history of living together.Some state has specific laws about roommates.

$40k saved up for starter rentalHey I’ve been saving up aggressively to get into rental investments I’m currently in college using gi bill and I will be for sometime .I wanted to use the va loan to get a house because rent is really really high where I stay also I need to get started now while I’m young . (1150 just for a room and bathroom.with everything else,like kitchen ect is shared with 4 other roommates located in 😅Prince George county Maryland) But the realtors told me I can’t do anything without employment verification like w2 or pay stub.even though I’m making good verifiable money every month from gi bill and my side business I have great credit also.

Firstly hello - long time reader and first time poster Some advice neededI have 155k (24 yrs) left on Primary mortgage at 4.1% (home worth 320-350k)If I cash out refi I potentially can take up to 100k out / drop interest rate to high 2's/vry low 3's and have a payment $200 up on my current monthlyI will make around 160-200k USD this year from my jobs (more if I buy a rental) and my mortgage is within $100 a month paid off by roommates (I cover the utilities which are $300USD a month)Question is with money being really cheap would it make sense to cash out 100k to have it and either stick it in the s&P500 or use it for DP on 2 or 3 investment properties?

You should screen the new roommates and all are on the lease. 

I want to build my rental portfolio rather aggressively so my plan is to live in a 3 bd unit and have two roommates.

There's always "rental arbitrage" -- perhaps you could look for a rental house with space for a roommate?