I'm also very open to meeting other investors and to exchanging ideas. 

The best approach is to set clear, written criteria, and then price the property at a rate that gets you enough applicants that you can find a few who meet your criteria reasonably quickly.

Be mindful that there are rules that the lenders want you to check off.Furthermore, there are other rules on the tax side where you want to normally be under to get the most tax benefits.The magic number in both instances is '14 days'Lenders want you to stay atleast 14 days to meet the secondary home requirement.The tax accountant normally wants you to stay less than 14 days or 10% of the days it was used as a rental to treat it as a rental and not as a personal residence.Best of luck!

Or maybe when I meet a certain amount of company revenue. 

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

You are generally correct that there is an annual exclusion for gift taxes that generally passes tax-free (of course, in all situations, exceptions apply and you have to meet all requirements to qualify). 

if so, let's set up quick meeting to see if we're right fitif not, i'll take a referral in SDThanks,Marko

If you rely on travel time to meet 750 hours, you're playing Russian roulette with the IRS.

If you pay more, you won't meet your metrics and will probably have negative cashflow and/or equity.You may have to make 10, 20 or even 100 offers to get one accepted at the price that meets your numbers.This is what all investors did BEFORE the Great Real Estate Crash of 2008-2010.

I can provide support of checking in on contractors, staging rental properties, walk potential leads to give you an idea of the property in person or what the area is like, meeting with agents, and drafting scope of work for projects.