Condos for instance will charge HOA fees, limiting your net cash-flow.A PM will run 14-16%+ as they charge a month's rent to place a tenant, take an extra month to turn a unit and charge you premiums and overrides for the work.  

That will protect you (to a limit) if you are ever sued.  

I'm trying to figure out if the hard money loan would act as a liability against the house if I was to try to refinance the house after the mortgage was paid off with the hard money loan. 

There is a big difference between accounting manager and account manager; account manager doesn't imply someone with an accounting background.It's better to find someone overqualified than someone who doesn't know the difference between asset and liabilities and operating and finance activities.

Too many might raise a read flag, but a business meal for a business purpose is not limited to they type of business relationship.

My eventual plan once I have enough capital raised for another downpayment would be to get another place and would only paydown the mortgage if the lenders say my debt to income ratio is too high.Your strategy should depend on your risk tolerance - everyone will have a different limit for the amount of risk to reward they are willing to take on.

Also income from the other units would be considered.Given what you are saying, you are likely working with limited income, so rate is going to be critical for you.

It's a bit of an art to pick out all of the items that are applicable and to make sure that you both get them all and also don't include something you aren't supposed to.For example, a monthly HOA fee would not be included in basis, but a paperwork transfer fee from the HOA would.You can also include title insurance, but not the liability insurance.  

They are going to push you to every limit to find your weaknesses. 

The benefits would be additional liability protection and additional deductions for management income.