I feel like its better to come out ahead every time I take a step, then to get beat down.

you have come out ahead?

Hard money lending business is all about patience.Things must be accomplished one step at a time and cannot be rushed.

Now that makes a lot of sense to go ahead with the deal.

If this is a temp fix and you are still going to need to replace the roof soon, why not go ahead and save the $4k and have the roof replaced.From your post it looks like this is a 4-plex building.

My biggest mistakes have all revolved around not screening as well as I should have and being in a hurry/careless about filling vacancies.John Wooden - "hurry but don't rush..."

Even then, it would be wise to plan ahead how to quickly pay off student debt.

She was renting it to family (Lesson learned) for the past 4 years, once they were gone we decided to go ahead and update it prior to selling, new bathrooms, carpet, paint, refinish cabinets, the works.

Josh,I went ahead and followed BP ... here's a screenshot of my dashboard after I clicked "follow" BP

@Jean Bolger absolutely don't pay someone who won't do the work to your satisfaction when you have told them ahead of time.