HOLD & REFI - The improved cashflow (I have one lender saying he could get me into a DSCR loan at 6.5% which would 3x my cashflow) is enticing, but I'm don't want to risk anything especially having been burned once and would prefer to be on the up and up. 

Here is some key information:Property recently hit the market and has 2 cash offers alreadyThe seller provided a pre-inspection report, which I shared with 2 different lenders, both think it may fail conventional financing due to potential structural and electrical issues (realtor thinks it could pass conventional)Seller has 100% equity but is behind on other payments (not sure of the urgency money is needed)This is my first attempt at an “investment” property so I’m new to thisI see 3 optionsMove forward with an offer using conventional loan pre-qualification-Not as attractive of an offer to the seller-Possibility that appraiser calls out structural/electrical issues that need to be fixed before closing, effectively causing financing to fail- Best terms and fewest loan fees for meUse a rehab style loan such as ChoiceRenovation-Even less attractive than a conventional offer to seller, but less risk of failed financing if appraiser calls out issues-Slightly worse fees and interest rates compared to conventional-Lenders tell me possibly up to 60-90 days closing in some cases, with red-tape for contractor requirements and draw schedules (sounds like the most hoops to jump through during rehab)Use a hard money lender-Most attractive loan option I can give to seller so I can compete-Much higher fees and interest rate for me-need to refinance into a conventional at the end of rehab (not familiar with seasoning periods but I think this is a factor as well)Which option would you do?

My main question is whether it makes more sense to go the seller financing route and pay off the principal in 8–10 years or stick with a standard 30-year loan.My thinking is that the tax deductions from a mortgage wouldn’t outweigh the potential equity I could gain over those 8–10 years.

How would you manage risk? 

@Emeka Okeke, while it can be debated, in my opinion, by far, one of the more simplistic ways to take action and learn the ropes of real estate investing, all while mitigating risk, is to house hack your first deal.

My out-of-state clients love it here because you can still find cash flowing deals hitting the 1% rule with lots of appreciation potential.

THEN, I plan to purchase the second home using a FHA or conventional loan (3%-5% down), for which I will likely pay the monthly cost out-of-pocket, maybe with some rental income support if it is a duplex.My concern is, I do not want to spend my savings or weigh down my debt-to-income ratio so much so that I cannot qualify for and pay the down payment and closing for the lending on the second home.Questions: - With the first home being multi-family, 75% of the rental income (or potential rental income initially) will relatively either maintain or boost my debt-to-income ratio from lenders' perspectives, right? 

Same tax situation and more likely higher potential to appreciate faster.

Again, if your $250k is true, and includes all the electrical upgrades, new plumbing runs, potentially new foundation pour (since I assume the existing garage slab is not capable of supporting a new two story house), I am guessing since I don't know the market, but assume you will have a lot of equity by completing the project.

He's helping me to narrow down a potential multi-family property that I will be house hacking, (the deadline I have given myself to be in it is May).