I also don’t want to exclude potentially the best contractor in the area and one who might go over the top to ensure that we get the best of everything since he has a unique relationship with our family (there are not a large number of recommended contractors in our area).

My option to pay off debt first is my own combination of Dave Ramsey advice mixed with the knowledge of BP.

@Jaysen Medhurst, I was able to qualify for a HELOC, If you don't mind looking at the terms.Assuming an appraised value of $225,0001stmortgage set up at $180,000 80% loan to Value (LTV)HELOC (Home Equity line of credit) set up at $33,750 15% (LTV)Combined loan amount $213,750 (95% of the appraised value)Interest rate 1st mortgage 3.875% 30 year fixed rate conv loanHELOC interest only ARM: WSP + 1% (3.25% Current WSP index + 1% = 4.25%) Principle and interest payment would be $846.43Full monthly obligation including Home Owners insurance ($100 per month) and Taxes ($100 per month) : $1,046.43The interest only payment on the HELOC assuming the full draw of $33,750 at 4.25% would be $122 (shown above) Total monthly obligation between both mortgages : $1,168.43~$25,000-26,000 would be the cash available from the HELOC at closing What this refinance accomplishes: ~$25,000+ out in cash for the real estate investment opportunities Escrow refund – should be a wash with what we are estimating we would be setting aside to start your escrow (~$1,200) and that is your money to do with as you please Creates a HELOC that you can tap into on an as need basis (during the draw period which is the first 5 years).

.), what each of those options offer as far as advantages and disadvantages, etc.2)  How to find good resources to help you find investments (seems like real estate brokers is the way to go, but I have absolutely no clue what to look for to find a good one as far as their background, let alone where to even look).3)  What websites, companies, and other resources are good to utilize.4)  How attorneys are involved, how to get them involved combined with brokers, etc. 

I am in a unique situation where one of my jobs provides an apartment, and utilities, for free.

I am pretty sure the appraisal for all 4 combined will come around $360k( the numbers worked for me still so I went for it, also I think I rushed :()Question 1 What should I give the bank as individual property prices knowing they will get an appraisal for each property?

This combined with the $100k overpayment puts you in a tough spot, especially after you factor in costs.If the numbers work for your situation and you are willing to take the loss then selling no w may be the way to go (how much time will it take to recover the loss by getting into other properties?).

To the best of my knowledge you won't get any of your social security benefits reduced since the rental income will not be included in the retirement earnings test but with a rental income that high, 85% of your social security benefits will be taxable so your social security will be reduced but not due to the retirement earnings test but instead due to crossing the "Combined Income" threshold.

And this is the best investment with a combination of passive income and higher ROI.

I started with 1 and the past few years I would buy a fixer upper and use the noncapitalized repairs and expenses on it and the noncapitalized repairs and expenses on the existing units and combine that with the depreciation on all the units to offset the gains on the ones rented.