Market circumstances might change, even if your intention is to flip the property, so think about your choices in case your initial plan doesn't work out.Market Analysis: To verify your predictions on future appreciation, growth in the rental market, or the effect of renovations on property value, do a comprehensive analysis of the market.Time frame: Evaluate the opportunity cost of having your cash invested in a non-performing asset and be realistic about how long you're willing to wait for the property to turn a profit.Investing in a property with negative cash flow can be a calculated risk under the right circumstances, but it requires a higher level of due diligence, market insight, and financial planning.

Making judgments and gaining important insights from experts with experience in your target market may be achieved through networking.You may confidently evaluate your possible investment and choose the best course of action for your financial objectives by carrying out extensive due diligence and making use of the information and tools at your disposal.

I would prefer to do the upgrades so that it gives the property a permanent higher monthly income and hence higher evaluation if I choose to sell. 

Evaluate whether the potential benefits outweigh the higher costs and risks associated with hard money loans.

Thoughts please.Hey Eric,First, I would start by making sure you understand how to evaluate/analyze buy-and-hold deals.  

Like you said, I will devote more emphasis on evaluating deals, making more competitive offers, and doing my due diligence when sourcing a contractor that can parallel my goals.

So, learn about that first - and a good point to start is a Nolo book (https://www.amazon.com/Every-Landlords-Property-Protection-Guide/dp/1413307000/) mentioned in the doc, it will explain about insurance, how to evaluate insurance, and then about property management, property code, proper leasing and all the way to LLC and hiring.My notes file are primarily on asset protection, and primarily for buy&hold, but they touch on many other rabbit holes that opens from that (insurance, property management, DOS, transfers, etc.).

I'm reaching out for guidance on a few points:Long-term Strategy: With the current losses, I'm evaluating whether I should hold onto these properties for the next five years or consider selling them.

Slaven,The only way to evaluate if you are paying too much for the coverage is to shop it.  

However, it's important to carefully evaluate the terms and costs associated with refinancing before making a decision.Ultimately, it's important to act quickly and decisively to address this issue before the next payment is due.