I purchased a 100 year old Four Square in March. The interior was redone in 2005. The exterior will need a redo in the next couple years. To date, we've tuckpointed the exterior, cleaned the existing gutters, built a new front porch and porch ceiling.

The house needs new windows that preserve the historic look but provide energy efficiency. The doors are also on my list as none are square and most of them aren't in the style of the home. The current siding is hideous vinyl siding over original (we think) lapboard. We can see some dry rot of existing soffits and fascia. We would like to replace it all. The gutters need replaced as they're old too but due to some architectural details they should be replaced when the new siding goes up. Finally we want to build and extension for a second bath and a family room with fireplace.

Does anyone have suggestions on how I might plan the order of these projects? It seems I should do all at once but given that I haven't hit the lottery, I'm limited in the number of projects to do per year. If I did windows/doors one year would that impact the siding folks?

Thanks in advance!