A 3-5% increase in that price range is around $25-$50 a month give or take.  

There are two to three markets I am interested in that I have some small relationships within that I could utilize, my hometown, my wife's hometown or a place I visit often for work.My questions concern the opportunity cost of learning the ins and outs of 3 different markets when the requirements of truly knowing the market increase the chances of success.Do I select one based on distance, the potential to cash flow or appreciate, or one that I may have more connections in?

I want the tenants to move out solely because the place needs a major renovation and subsequent rental price increase.

I'm finding the hard part is more finding properties that are in a good location and also don't have restrictions on short term renters (either hoa or local regulations).I've reached out to owners with the same basic offer (increase rent, cover repairs up to a certain amount) and most people are hesitant to even discuss it, so i think it's a sheer numbers game and being ready to buy a property when one shows up that matches my criteria

I am a 25 year old South Denver native and have worked as a carpenter for my fathers residential remodeling company on and off for the last 10 years (throughout High School and College), since graduating college I have become increasingly interested in the business side of residential homes and have therefore been a licensed Realtor for 18 months now.

Due to the increased wear and tear from more occupants, is it reasonable to ask for more rent, such as 2800 or 3000?

Has anyone seen success from online advertising, or do  physical yellow letters increase the perceived legitimacy of one's investing operation to a prospective buyer?

Our plan is to get in, rehab the property, increase rents, decrease expenses and of course increase the NOI of the property. 

You can give a flat amount, or pay the difference between this months bill and last mo ths bill (you are assuming any increase is due to you) or divide his months bill by 30 days, and pay for the days you were there (if you do work for 2 days you pay 2/30 of his bill)

You can offer then less then the loan default value, and as time passes, their motivation increases.