I am getting pretty frustrated because every offer I have put on a property with the intention of renovating has not been accepted and when I find out how much it ended up going for my offer is always significantly lower even though most of the time I go in above asking price.

My main challenge as a part-time investor is being lower on their buyer's list but that just logical business.

Quicker close, lower closing costs, and better rates....

Duh - try lowering the price. 

Here is the quick pros and cons on both.Gloucester: Pros -  Good tenant pool, strong schools, most houses have public utilities, consider the more desirable area of Sicklerville by the local populationCons - higher taxes, pulling permits takes the full ~21 days, higher home prices, overall thinner marginsWinslow:Pros - Lower cost houses, rental friendly township, strong demand for rentals, slowly up & coming in certain neighborhoods, lower taxes, overall fatter marginsCons - Lots of C and D neighborhoods and lackluster tenant pools, poor schools, the more east you get the more well/oil/septic you find, considered less desirable area of Sicklerville by the local populationBy the numbers both GC and WT have similar rent rolls only off by $100 to $200 depending on the house type, therefore Winslow you will net more but have a slightly riskier houseAgain this is just a general view, you'll want to look at each sub-division as there are massive swings within each twp (Ex: Brittany Woods compared to Cobblestone in GC)

I can put in the extra cash, its just an annoyance and lowers my ROE in the intervening time.

Well $1,000 is really nothing, so the lower offer might have a better lender, better agent, better terms etc. 

Lower taxes, and prices are not as inflated as Westchester.

Air BnB has 6 times the users and platforms like Booking.com can acquire customers at a much lower acquisition cost.

Obviously regulations in the US are much less complicated, taxes lower, laws much more landlord-friendly and profit margins higher than in Germany.