These owners are usually more sophisticated than the typical homeowner and your mailings need to reflect that. 

It also requires gaining a level of sophistication and knowledge that not everyone has the time, inclination or ability to do.

Ultimately, you want a CPA and Quickbooks...that is the magic combination.If you are looking at financial modeling or more sophisticated solutions, we use a VA Firm called UpWork...some pretty bright folks out there. 

Caribbean workers don't seem to be very dedicated and think nothing of missing a day of work.Mexico, Central & South America the biggest challenge is finding workers who's perception of their English matches reality. 

If you want to have a better return on equity (which is what most sophisticated investors want) you get two and leverage.My article on return on equity - https://www.biggerpockets.com/...

Sophisticated investors with a lot of time, a lot of real estate experience, access to cash and a large portfolio, would be wise to give it some thought. 4.  

My first goal is finding a place for my wife and our two dogs to live and possibly flip at a later date, but after that I'd like to begin building a portfolio of investment properties and tenants because Ive recently gotten a new job that allows me to save a decent (at least to my perception) amount of money for investing.

Good areas vs bad areas is a different question and takes stats out and adds opinion & perception.

My question is geared towards LP's perception and how withholding/paying distributions made them feel about the sponsor that they invested with.

For entry level investors it can be tough to find properties that are listed before they get picked up by institutional investors with sophisticated tools and algorithms.