I'm  perpetually on vacation.. flying to San Antonio today, just got back from Golden CO last week.

For beginners especially, the 'work ON your business not IN it' rhetoric is a good way to go broke and be perpetually frustrated.    

Or should I perpetually add to my reserves for a particular property?

They have perpetually continued a decent into the suck since first being aquired by homeaway and then more precipitously when expedia reared their ugly heads.

I full intend to claim it but wanted to make a general stereotypical statement that when someone makes a relatively small amount of cash on the side, they don't claim it.

I think I learned a valuable lesson today and couldn’t agree with you more haha but every bit of it is important because any honest “wholesaler” (which I’m now no longer sure the meaning of the word) can see the pain points and strive to be the opposite of the apparently stereotypical wholesaler mold and just are there to acquire and move solid deals with realistic numbers

@Robert BladeIn general, lenders want to see monthly housing debt of no more than 28%-33% of your income and total debt of no more than 38% of your income.The rental income should be ~80% supposedly your current rental income to account for vacancy etc, If you are government employees guarantee for perpetual income want to work another 10-15 years you can be a bit aggressive on total debt. 

Based on your numbers and the fact that this is a condo unit in a rural area with no HOA, my conclusion would be that this is a perpetual money pit.

I recently got hired at a stereotypical office job that very quickly made me realize how much I crave financial independence.

If you don't think that you can do this, then this will be a perpetual problem for you.