And is this a smart choice? 

As you can see, I lose an average of 1100 a month over this house.I am wondering if a short-term rental could be a better choice for me. 

Cities with limited land for expansion have higher appreciation than those with abundant, low-cost land where new construction is preferred.

Six-unit apartments are an excellent investment choice, and I’d be happy to help you explore options that align with your goals.Looking forward to hearing from you!

This can be very expensive and is usually the worst choice because you can't justify the cost.2.

As far as benefit to the seller goes, @Matthew Paul I think you are probably right on the money and regardless of whether they would have preferred to stay in this house rather than move, it is likely providing them some excellent cash flow; and I'd be hard-pressed to come up with a deal that serves both parties better than the current situation. 

I think this is a calculation a lot of homeowners are making right now--especially if they have a low interest mortgage, equity, and their house will cashflow as a rental.The choice is a personal one of course, but I think your future self will thank you if you pull out some equity from your existing home with a HELOC for the downpayment on the next house and a cushion renting your current home, use a property manager as you have other things to do, and buy the next house and do the same thing again.

Buy box: Location: Approx. 30 min drive to Boston Heights, for workNeighborhoods: Decent walkability score - not far from shops/restaurants/trendy neighborhoodsIdeal tenants: Close to hospitals/universities/schools for professionals/students/familiesBudget: $175-250K - Buying w/conventional loan, 5% down/ approx 20K reno.Property type: MFH 2-4 units - preferably side-by-side, with a yard we can fence for our dogUnits: 3+/1+ - better if 1.5/2 bath per unitTimeline: Plan to live there for 2 years, but possibly only 1 year if we find another investment opportunityGoal: Focus on appreciation - would like to see cash flow in year 2-3 (the year we move out), including overhead (Vacancies, Maintenance, Utilities) and budgeting in PM if eventually we don't manage ourselvesValue add: Opportunity for some forced appreciation, but not a full reno - cosmetic upgrades and updating kitchens/baths while we live in one unit.

Quote from @Amanda Nelson: Hello - I found a very compelling investment property and the agent and her preferred lender are suggesting that the VA loan currently on the property is assumable by a real estate investor.

To make the most informed choice, get a Cost Seg feasibility analysis (free) which illustrates the expected tax deductions and then assess how those deductions impact your tax liability, based on your tax profile.