In regards to negotiating with the HOA that should be a No, I would assume if he owes $8k in back dues there's most likely a lien on the property if the HOA is doing there job correctly to insure they get paid.

After years of sticking with a job I hated and saving up enough money to feed my family for a little while, I decided to quit my "safe and stable" job to chase the dream!

I hired  a property manager thinking they could do a better job finding tenants - nope.

I have excellent credit, a DTI of less than 25%, and a well paying job at a business I've been at for over 5 years.

I'd recommend as @Theo Hicks said to stick to a weekly report from your PM and then calls on as needed basis.Before you jump into this investment, ensure that the numbers work and the overall investment makes sense = low vacancy, demand is high, town population is on the rise, jobs are available and accessible, etc.Best of luck!

We both have good jobs and we're almost living on one income.

These aren't issues that are specific to flipping and should be a primary focus for any real estate investment - The bottom line is that you made a profit despite the challenges you faced - and congratulations for that - but it seems to the bystander that you gambled with another investor's money while investing very little of your own - you put yourself in the position of a teacher or mentor when in fact you are not extremely experienced in the business of flipping - consider how you would feel if you lost a portion of your partner's investment....Today I am closing on the purchase of my 15th flip for the year, and I wouldn't dream of taking on an investment partner who wasn't equally experienced and had an equal say in the decision process.Good Luck with your future projects and Happy Investingjeff 

(I would also pay for the monthly rent via my savings/day job – in speaking with the owner, he said it would be a minimal amount because the property needs work).I don't know exact numbers on what the rehab will be, but I've been doing some research on the costs and am working from an average at the moment, as I look up what basic rehabs for kitchens, bathrooms, electrical, plumbing, new roof, etc. could be.

My dream is to buy distressed properties, rehab them, rent them out, leverage other people's money to scale up, and hold my properties forever - basically the BRRRR strategy that @Brandon Turner and @Joshua Dorkin teach.I'm glad I found Bigger Pockets - a great resource.

Matt Avila I would recommend keeping the day job.