And keep in mind that the rate on the 2nd lien will likely be 10-12% so depending on the cash flow it might not actually yield that much cash to you at closingMore importantly, it's just more debt so ultimately it sounds like you need an income-producing event to actually improve your situation and avoid some of the consequences that you mentioned

I only mention this because I noticed your mention of Furnished Finder, which is the only platform I list my MTR, and FF caters to 30+ day stays. 

As others have mentioned, you may need to have some patience and see where it goes.  

Why haven't any of the BP podcasts mentioned this?

But Brandon Turner mentioned Asana is what his company, Open Door Capital, uses (in BP Episode 479). https://www.biggerpockets.com/...

Quote from @John Williams: Quote from @Daniel McDonald: @John Williams like Bruce mentioned area is going to play a huge part. 

Aging reports would be another avenue to explore, but again, may not even have these.Lastly, while maybe this property is in a desirable area of town with strong demand from highly qualified tenants, but I get the impression this is a rough part of town, with very limited demand from tenants.

Actually, a friend once mentioned a unit in Eugene that had to be re-leased after a nasty storm tore off part of the roof.. it’s gritty, hands-on stuff like that which rounds out your perspective.At the end of the day, you don’t need a flawless blueprint to get started.

As you mentioned, it might be difficult timing the sales of each of properties where you can achieve a combined exchange (multiple properties into 1 property / or a few properties).Just a quick note that may be helpful - I work with a group of investors that can help with a combined exchange into a single property and will buy it back once you've found a replacement propertie(s) as the final destination for your capital.

As mentioned elsewhere, breakeven on cash flow is not the same as break even for taxes.Let's make some assumptions:Rental income = $1000Mortgage payment = $400 - but $300 is interest and $100 is principalOther expenses (repairs, advertising, utilities, etc) = $600Depreciation = $250The above scenario creates a break even from a cash flow perspective, however the tax scenario looks like this:Rental income minus the mortgage interest (principal is not deductible) minus the other expenses minus depreciation looks like this:1000-300-600-250 = $150 LossIf your income is over $150,000, then you cannot deduct that loss, but you can roll it over to future years.