We’ve found a niche area that fits our budget and personal vision, and it has usually taken a few months of regularly analyzing deals to find something that works for us.

However, if you know and have a relationship with the person/team that will be doing the rehab for you in your absence and trust they have your vision in mind then you are in a better place to start. 

I wouldn't worry too much about it, if you have a competent CPA or bookkeeper they should be able to review your books and within minutes have a strong grasp on who gets a 1099 (spoiler alert, not every contractor gets one, I'll be annoyed if I get one since I'm structured as an S corporation) and the amounts to report.1099 filings are usually a loss leader for us, so if you're working with a professional make sure you take advantage of them filing everything for you.

I am not sure if it was just my market or more on their end but at the end it was a pretty big loss for us, so we cut it. 

Hi Jeff,Sorry for your loss. 

If you are in this business long enough you will undoubtedly arrive at situations where taking the small loss even if not fair or warranted based on the circumstances is best if it keeps everything moving and avoids more costly delays, liability and inconveniences.In this case, if you withhold the $2K, you still have to find someone to complete the work to your satisfaction.

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. 

Hi Nedim,It sounds like you have a clear vision of your goals, which is great!

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

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.