As an out of state investor, am looking to work with wholesalers, agent or bird dog who can walk the ground .

Any thoughts/advice for small investors trying to get into larger properties?

Most of our newer investors approach 2-3 lenders to discuss loan options.Some lenders recommend making your financing inquiries within a 45-day time period to avoid larger drops in your credit scores.All the best!

Because I need cashflow proceeds to start being withdrawn in 2 years and not today, I'm looking for how I can build up the empire with a larger portfolio with continued investments beyond the initial $250k now.  

For C to B-Larger developments announced nearby-Increased activity in new construction-Building of commercial retail in or near the neighborhood. 

You have the tools and mindset that work with larger scale commercial so I would network until you meet someone who may let you run some of their deals with them and see what they look like in person.

Scotia Bank in Costa Rica will allow you to open up an larger account as 'business owner' if you own your properties in an LLC but the process of opening an account is much more difficult. 

Should you add a playground or dog park, or would your money be better spent on putting in gated access?

Brian,We see a lot of "residential" investors taking on larger deductibles than they have in years past, and even more so as we see rates increasing in a hard insurance market. 

There are new construction homes about 2-3 miles away going for 190-200,000 but I think they may be a bit larger than what I am building.