If they have lived in the property for two of the five years before the sale, they have an exemption for up to $500K in capital gains. 

I would be concerned if I invested in the bottom five cities, New York, Miami, Cleveland, Washington, and Chicago.

Here are some basics on the property.SFR RentalLong term (3yr) tenant pays $1350/mo + all utilities (tenant is local school superintendent)Owner possibly refinanced at $100k in 2003.26 acres2 /11 1/4 story capeWaterfrontDetached 1 1/2 story garageTown Assessed Value: $122,300Actual resale value: potentially around $150k Deeded access I have put in 10% management, 8% vacancy, and about 6% others (capex, maint, etc.)So here is what I would like to send his way for a seller financed offer with no money down: Seller financed at 5% (30 yr amortization) with a 5 year balloon payoff payment Balance payoff payment at 5 years (~$91,829) Early payoff <24 mos = 10 points ($10000)Early payoff >=24 mos <36 mos = 8 points ($8000)Early payoff >=36 mos <48 mos = 4 points ($4000)Early payoff >=48 mos <60 mos = 2 points ($2000)Option for buyer to extend payoff date up to 15 years (within 6 months of payoff date, at a cost of 2 points.)Buyer to pay all title, recording, transfer fees etc.Total Interest Paid (If paid in full at five year mark):$24,038Total Sales Price with interest (If paid in full at five year mark) : $124,038Keeping in mind that we make money on the purchase, I would like to offer a fairly low purchase price that would help me get my foot in the door, and continue to give him monthly cashflow and delayed capital gains.  

Houses that would have cost 105k five years ago are going for 180k and up today.

Shop around for utilities if you are paying for it.Shop around for dumpsters line up the contractors to do all maintenance requests or upgrades you need to do.get ready to Install motion lights outside prepare ownership change letters to tenantscopies of keys copies of all leases (should have got in DD)Ask the lender and title company to provide you with the final Settlement statement so you see which other costs to expect. 

Easy access and walking to a nice downtown.Units: 4 - 2bd/1ba Utilities- All electricAsking Price; $300KCurrent Taxes: $8100Utilities: $275 per month Insurance: $200 per monthAverage Annual Costs Including withdrawals for self-managing fee, Taxes/Insurance and Utilities- $26k per yearCurrent Rent: 3 Units $850, 1Unit- $800 per unit (tenant pays electric)Comparable local units for 2br - $900-975All questions and comments are welcome.Thanks in advance!

How long have the tenants occupied, what they pay for rent, do they have any deposits, are pets allowed (or have they ever been allowed), who handles lawn care, what does the owner pay for utilities, have there been any lease violations or noise complaints, do the tenants pay on time...Those are some examples.

And BTW I, or anyone, can get your social security number and much more, in about 10 minutes, for less than $20. 

I purchased my first property utilizing my VA loan however I did not buy it as an investment or with the perspective I have now.

It will just take five minutes:https://www.surveymonkey.com/r/C986XM2