It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

Quote from @Stephanie Menard: I rented a furnished home in Las Vegas, NV, to a fully screened tenant.  

We're currently renting downtown and looking to get started as first-time home buyers in an owner-occupied duplex situation to start our path in rei. 

However, if i would take 100k home equity on a rental A (ex. 100k) and use 50k each (same as above) for 2 rentals (B & C).

This is the reason homes are so much cheaper than cost to build.

Our home is heated with propane.

I understand it become tad difficult to refinance since some lenders wouldn't lend on the home in trust, but is it easy to sell a home in a trust, just like you are buying in a trust?

I own a home which I’m currently living in and planning on making a long-term rental property as well once I move out.

@Sang Kim- thanks for clarifying you are trying to get a commercial loan ...this is a  completely different product than a home loan ...You still should be able to  locate and obtain a good commercial loan  without  having to pay any fees upfront  ( other than possibly paying for the appraisal after the  loan has been  approved )

Purchased for $69,000, I tackled everything from a new roof to interior updates, transforming it into a move-in-ready home.After months of surprises (and a few headaches), I sold the property for $145,000.