I want to learn how to have a reasonably good estimate of repair and upgrade costs so I can do post-renovation comps for them.Knowing it's tough to overcome, I'd also like to learn how to deal with the challenges presented by squatters who refuse to leave rentals

What challenge did they overcome with financing the first few deals and how did they overcome?

Cabins that have nice amenities such as a good view and privacy (and other desirable amenities) can overcome the location to some degree.

My hurdles to overcome before making my first investment include figuring out financing, learning to understand the market I am investing in, and developing an understanding of how to structure partnerships and/or syndications.I am looking forward to making meaningful connections on bigger pockets, and digging into the forums and educations materials available here.

To help overcome this I started an LLC for future acquisitions, and have been buying in it. 

Meanwhile, the mistakes made while overcoming the learning curve can be expensive.I never said Michael should hire a PM, I simply asked if he was equipped to self-manage.

It can require extreme effort and hard thought to overcome.

Work through your learning and problem solving TOGETHER, in a methodical manner:what's the problem to be solved (and each should not be compounded with extra conditions).list all possible solutions you can find (without discarding any due to bias, personal business ideas or obvious negative effects).then find and list all pro+con issues related to that solution you can.SAVE your work in a binder for quick access later and to visibly demonstrate just how far you both have come.There's no rocket science in REI, but limited exposure to business concepts, contracts, accounting, marketing can ALL be overcome and your partnership will grow as a result.

Some of the most inspiring stories are from those that have overcome obstacles to be successful, and are moving up the ladder.

Ive taken on challenges, overcome obstacles, added onto my work load so I can learn and grow as person.