Simple green space and seasonal food vending in the heart of town would seem to be a fine plan, entirely within the zoning ordinances as they currently exist (although a restroom facility may be necessary for long term).  

I currently am getting $675 a month positive cash on my paid for rental and would like to receive at least $300 a month on future properties that are financed.My question is, what would be the best way to leverage this property and will the lender consider me a seasoned investor and work with me ?

In my experience companies get specifically touchy about this subject during hurricane season.

Your management costs are greater (25-50%) if you have it managed, And your window for income generation is often seasonal.  

Im a young new investor in the DMV area who is currently seeking any seasoned investors looking for assistance in their flips.

It is difficult to tell how new or seasoned the loan is and how the loan was performing prior to your purchase.  

Tip: never expect to get much done during deer hunting season.

Or like @Rich Weese , you just strategically place your properties around the countr(ies) so you get all the best seasons and everything you like ;)By the way Rich, I traded an old truck of mine that couldn't pass smog for a coin-op washer and dryer on the deal I finished in July of this year.

We also participate in storage auctions, but that's for another forum :)Whew, I'm going on pretty long... sorry!

The Quartz counters in the bathroom and kitchen got installed today.Major Structural: -100% New Electrical (Wiring, Faceplates, Switches, Fans, Exterior Panel, LADWP feeds, etc) -100% New Copper Plumbing -New Sewer Drainage pipe to LADWP -Brand New Roof (1st layer, House&Garage) -Brand New Gas Water Heater (and moved from kitchen to outside of house) -All brand new windows -Brand New Doors -New Wood laminate floors throughout entire home -New lawn sprinkler system -Custom landscaping with new sod, colored stone, colored mulch, & plants/trees -New wood fence-Crown Moulding Install-All new baseboard installedEntertainment/Convenience Features: -New pantry -Laundry hookups in garage-LED Lighting & Bulbs Throughout -Whole Home Ethernet (Network) Pre-Wired -Living Room Sound System Pre-Installed (4x 6” Spkrs, 1x 8” Center Spkr, Subwoofer Hookup) -Living room HDMI pre-wired for wall-mount TV -6x Recessed Lights in Living Room -Each bedroom has 4x power outlets minimum -Firepit in backyard -Elevated concrete slab section for BBQKitchen: -Custom tile floor w/ pattern -Cappuccino Wood cabinets -Quartz Stone Slab Counters -Spice Racks -Trash storage drawer -Enclosed Surround for up to 36” Fridge -Recessed light over sink -Dishwasher hookupBathroom: -6ft DUAL Master Vanity -Cappuccino Wood cabinets (matching kitchen) -Quartz Stone Slab Counters (matching kitchen) -6 Storage Drawers plus 2 main under sink storages -4.5ft mirror -Custom tile floor -Custom shower/bathtub tile surround -2 Recessed Nooks w/ Interior Colored Glass