If I can afford the financial loss of it not being rented those months (2K mortgage) then maybe it's at least worth trying?

Plus, Zillow, Rentler and the other real estate platforms tend to have all sorts of unnecessary hoops to jump through for landlords, and I find a lot of their design very un-intuitive (I remember spending waaayyy too much time just trying to figure out simple things in Rentler).  ...why can't they make it easier?

@Brody Veilleux Loss harvesting in real estate allows you to offset capital gains by selling a property at a loss, which can also offset gains from stocks or other investments.

Realistically, many properties that go to auction may be in such bad shape that they don't justify the high bidding amounts, leading to losses as I mention above. 

This is because they didn’t budget properly and rent wasn’t high enough to cover actual expenses (repairs and maintenance, cap ex, vacancy and loss, tenant damage and turnovers, etc don’t expect to have any money left over after all of these expenses are accounted for if the rent is less than $1,500/month). 

Make sure you understand the basic math, what qualifies as a good investment, how to manage your investment and prevent losses, etc.I would start with Set For Life by Scott Trench.

Not sure is selling individually is worth the headaches or count my losses and sell as a whole, if there is any? 

It sounds like this may be a loss but I am sure you have learnt from it.

I think I could address more, but it's unnecessary.

I run sum numbers for you please see comments below before refinancing and post refinancing .If I were in your position, I would approach it as follows:Initial Investment Assumptions: Market Value: $360,000 Purchase Price: $360,000 Equity: $0,000Financial Breakdown: Hard Money Loan (LTV 100%): $360,000 Interest Rate: 10% (30-Year Amortization) Monthly Payment: $1,995Upfront Costs: Origination fee (1%): $3,600 Closing Costs (3%): $10,800 Renovation Costs: $10,000 2 Month of Carrying Costs During Renovation: $5,390Total Upfront Required: $29,790Total Capital InvestmentPurchased price $360,000 Upfront Costs $29,790Total: $389,790To make this investment work, you need to rent the whole property for at least $3,165/month, refinance it let say after one year with 5% interest with a traditional mortgage.Year One Rent: Monthly Rent Income: $3,165 Monthly Rent Losses during renovations (2 Months): -$6,330 (-$527/month distributed over 12 months) Total Rent Income: $31,650 per year => $ 2,638 per monthMonthly Expenses: Hard Money Loan Payment (10% Interest): $1,995 / per month interest only Property Tax (Assuming $3,000/year): $250 per month Property Insurance (Assumption): $100 per month Utilities (Hydro, Gas, Water): $292 per month Assuming 0% Vacancy first year Assuming 0 % Repairs & Maintenance first year because unit has been recently renovated Total Monthly Expenses: $2,637Monthly Net Cash Flow: $1Post-Renovation Refinancing Strategy:So far, we’ve purchased the property, completed renovations, and rented it out.Next, you can approach the bank for a refinance to consolidate your initial investment of $29,790 plus your 360k debt into a mortgage.