Hi SB Buyer,
To answer you question regarding insurance costs, in a condo your insurance is included in your maintenance fee, you would only need interior insurance which would be just a few hundred dollars per year. A townhouse would need just a little bit more insurance depending on the HOA, but not the same as a single family home, which will not be an option within this price range.
I will tell you, as the others have, that the budget and HOA are very low for these areas and you may become frustrated with the search.
There may be some misleading listings on some of the sites such as here on Trulia because of short sales or auction ads. The truth is, about 3 years ago we had a good supply of decent priced properties, but the market has changed and it is not a "low-ball" offer type of market, and we have a short supply of inventory.
If you want an honest discussion of the market and your options I would be glad to speak with you at your convenience, because you may become frustrated by the many answers and options you see.
South Florida Brokers