Should I continue to pursue the original house deal by deducting their estimated repairs?

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

Quote from @Fred Scott: Sunrise Capital Investors - Mobile Home Park Investment FundI've seen a few posts about them here but none of them actually talks about what the actual annual returns have been.They are advertising heavily for passive tax deductions which is fine but what are the actual returns over a period of (say) five or ten years?

Watch out for what gets deducted in home warranty or concessions but those will be in offers you accept. 

That will cost us about $4.8K out of pocket (our insurance deductible under our Rental Dwelling policy). 

@Brendan M Hornung If you purchased a subject-to (sub-to) rental property, filing taxes correctly is key to maximizing deductions and staying compliant.

Quote from @Eduardo Perez-Borroto: Since the HELOC was not used on improving the home you cannot deduct the interest, nor use that to offset your capital gain.Would adding a battery bank system to my solar panels count as home improvement? 

You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well. 

I intend on sending the tenant a bill for the exact repair cost as "additional rent" (per the lease) instead of evicting in the winter and deducting from the security deposit.

Here are some quick stats to consider:Tangible Asset: Real estate is a physical asset you can see and touch, which can provide peace of mind.Cash Flow: About 33% of homeowners rent out their properties, generating consistent income through rent.Appreciation: Real estate appreciates by about 3-5% per year, while the stock market averages around 10% but with more volatility.Tax Benefits: Investors enjoy deductions on mortgage interest, property taxes, and depreciation.Control: You can actively manage and improve your property to increase its value.Just take it step by step, and you might find real estate is less risky than it seems.