It is currently a glorified finished attic with little room- Use addition and raise it up and extend it to the side of the home for more finished space and room for deck, washer/dryer room etc- Make the living space as functional as possible with the added sqft- Add outside living structures like deckThis is a fairly wealthily area and I want to maximize my ROIWhat are some things you recommend for a large scale project like this and what are some hurdles ?

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

There are many horror stories on collecting for damages from OTAs including a current thread on BP where guest left doors and windows open upon exit that resulted in frozen pipes.  

I currently live in Southern Maine and am looking to construct some kind of new project rather getting into rehabbing existing residentialProposed Land Budget 100-200kConstruction Budget: 400kAll in 500-600k.I have found that if I do the site work myself including clearing, septic and digging the foundation is that i can sub contract out either steel or a Lester style building (50x150) for around 300k installed with insulation and power , divided into three 2500 square foot units. 

Some examples of properties with high asset reclassification include medical clinics and hospitals with technical machinery and labs, grocery stores with machinery, shopping centers with rainwater drainage systems and large parking areas, industrial manufacturing facilities with advanced equipment, apartment buildings in suburban areas with swimming pools, golf courses, tennis courts and large parking areas for tenants.Here’s a list of the average amount of assets that can be reclassified into shorter asset life classes based upon the type of property.

New unit: 4-unit multi family in which 3 units (with existing tenants that will carry over from seller) will remain investment; I will move into (currently empty) 4th unit AND USE as primary residence with primary mortgage.

Places like San Antonio might present more favorable cap rates, from what I read in Forbes recently.Refinancing could free up equity if today’s loan terms are more attrative, though that depends on current interest rates and the property’s updated value.

Quote from @Shaylynn O'Leary: Hello, I' m a newer investor in the process of getting my first property under contract near where I currently live.

I agree, shorter-term plays are tough in the current environment, and patience paired with a strong strategy often leads to success, unfortunately this is a strategy that a lot of real estate investors don’t really have the experience and the patience to follow.

Right now i am currently in the Georgia Area