Certain states do not allow your primary to be foreclosed upon for other judgments (for example I believe florida is one of those states) - they can still get a judgement against you for the delta though.But yes this is a concern that every person should realize, which is also why you see many of us here on BP telling people to make sure they have adequate down payment and reserves before they get into something they have never done before.

In real estate you have to invest a lot of time and money trying to find the right person that "clicks" with you in order to get a client to work with you.

Purchase price: $380,000 Cash invested: $19,648 Sale price: $485,000 Not really a portfolio investment as it currently my personal residence, but I'd still consider it an investment.

Explore FHA or conventional loans based on your eligibility and current market rates.For a medium/longer term strategy, keep an eye on interest rates for potential refinancing opportunities for Property 2 when rates are more favorable. 

My goal here is to keep it real. 

Keep that in mind whether you're managing yourself or you hire a company to do it for you.  

Again, you will certainly lose some, but may keep some.  

Ideally something that is on web/app that'll allow me to keep track of different items come tax time. 

The IRS generally allows deductions for second homes if you use the property for personal use for more than 14 days or 10% of the days it's rented, whichever is greater. 

My current primary ( scenario 1) Keep the primary for the life of the loan ( current rate is 4.5 so i dont see my self refinancing anytime soon)current home value 1,150,000Loan amount 935,000appreciation estimate 5% per year after a 28 year hold and the house is paid off I would have a house worth 4,312,000$my current mortgage is 6125$ ( piti) included My second option( scenario 2) Sell the house, walk away with $150 ,000 ish in hand and put that into a low cost index fund Rent a house elsewhere for about 3000$ ish and take the extra 3000$ im saving everymonths from not having to pay my mortgage and puting that money in the index fund as well I ran the numbers on both of these scenarios and doing what I mentioned above would break even at about 28 years meaning my stock account would be worth 4.3 million just like my house would , but the only is that holding a house for 28 year would mean 28 years of property taxes, loan interest ,home insurance and repairs etc whick I calculated to be about 1,200,000$ at minimum which raised my eyebrows to say the least Also i understand that each of these options ( stock market vs real estate ) will have there tax consequences ( long term capital gains) so any thoughts on that would be appreciated as well.